Ethyl Bromoacetate Research Articles

Microwave-Assisted Hydrolysis of Ethyl Azolylacetates and Cinnamates with K2CO3: Synthesis of Potassium Carboxylates.

In this study, the hydrolysis of ethyl azolylacetates and ethyl cinnamates using K2CO3/ethanol under microwave irradiation was developed. For this purpose, ethyl azolylacetates were first synthesized by nucleophilic substitution between the corresponding azole and ethyl bromoacetate under sonication at 50 °C for 3 h, yielding derivatives with 10-92% chemical yields, while ethyl cinnamates were obtained by a microwave-assisted Horner-Wadsworth-Emmons (HWE) reaction of triethyl phosphonoacetate with a variety of aryl aldehydes at 140 °C for 20 min, yielding derivatives with moderate to high yields (67-98%). Initially, the optimization of the hydrolysis reaction was performed using ethyl pyrazolylacetate as a model starting material while varying the temperature, time, and base equivalents; the best results were achieved by carrying out the reaction at 180 °C for 20 min with 3.0 eq of K2CO3. This simple and greener method facilitated the synthesis of potassium carboxylates in moderate to high yields, 80-98% for azolyl derivatives and 73-98% for cinnamate derivatives. The structures of all potassium carboxylates were confirmed by FTIR, 1H, 13C NMR, and HRMS.

Mapping of Some Further Alkylation-Initiated Pathways to Polyheterocyclic Compounds from Indigo and Indirubin.

The reaction of indigo with two equivalents of the electrophile ethyl bromoacetate with caesium carbonate as a base result in the formation of structurally complex polyheterocyclics, including a fused spiroimidazole and a spiro[1,3]oxazino derivative, together with a biindigoid-type derivative, through a convenient one-pot reaction. Further assessment of the reaction using five equivalents of the electrophile gave rise to other molecules incorporating the 2-(7,13,14-trioxo-6,7,13,14-tetrahydropyrazino[1,2-a:4,3-a']diindol-6-yl) scaffold. The reaction of ethyl bromoacetate with the less reactive indirubin resulted in the synthesis of three derivatives of a new class of polyheterocyclic system via a cascade process, although yields were low. These compounds were derived from the parent indolo[1,2-b]pyrrolo[4,3,2-de]isoquinoline skeleton. Despite the modest yields of the reactions, they represent quick cascade routes to a variety of heterocycles from cheap starting materials, with these structures otherwise being difficult to synthesise in a traditional stepwise manner. These outcomes also contribute significantly to the detailed understanding of the indigo/indirubin cascade reaction pathways initiated by base-catalysed N-alkylation.

Synthesis and Molecular Docking of some new Thiazolidinone and Thiadiazole Derivatives as Anticancer Agents.

New sets of functionalized thiazolidinone and thiadiazole derivatives were synthesized, and their cytotoxicity was evaluated on HepG2, MCF-7, HTC-116, and WI38 cells. The synthetic approach is based on the preparation of 4-(4-acetamidophenyl)thiosemicarbazide (4) and their thiosemicarbazones 5 a-e, which are converted to the corresponding thiazoldin-4-one compounds 6 a-e upon cyclization with ethyl bromoacetate. The thiadiazole compounds 9 and 12 were obtained by reacting 4-(4-acetamidophenyl)thiosemicarbazide with isothiocyanates and/or ethyl 2-cyano-3,3-bis(methylthio)acrylate, respectively. The thiazolidinone compounds 6 c and 6 e exhibited strong cytotoxicity against breast cancer cells, with an IC50 (6.70±0.5 μM) and IC50 (7.51±0.8 μM), respectively, very close to that of doxorubicin (IC50: 4.17±0.2 μM). In addition, the anti-cancer properties of the tested thiazolidinone and thiadiazole scaffolds were further explored by the molecular docking program (MOE)-(PDB Code-1DLS). Compounds 5 d, 5 e, 6 d, 6 e, and 7 have the best binding affinity, ranging from -8.5386 kcal.mol-1 to -8.2830 kcal.mol-1.

Synthesis, Biological Evaluation, and Docking Study of a New Series of Thiophene Derivatives Based on 3‐Oxobutanamidothiophene as an Anticancer Agent

AbstractHerein, the constructing synthon 3‐oxobutanamidothiophene derivatives 2 a and 2 b were synthesized and utilized for building a wide variety of pyran, thiazole, pyrazole or pyrimidine ring heterocyclic compounds that can be used as anticancer medications. 3‐Oxobutanamidothiophene derivatives 2 a,b were coupled with 4‐substitutedphenyl diazonium chloride to produce the corresponding hydrazones derivatives 3 a–f. Various thiophene‐pyran derivatives 4 a,b were synthesized through the treatment of thiophene components 2 a,b with different arylidene‐malononitrile. 2‐Aminothiophene derivatives 5 were prepared via Gewald's reaction between 2 a,b, elemental sulfur, and various activated nitrile derivatives. The 3‐oxobutanamidothiophene derivatives 2 a,b were reacted with PhNCS and the potassium salt intermediates 6 a,b with ethyl bromoacetate to pick up the corresponding thiophene‐thiazolidin‐4‐one derivatives 7. Treatment of the conforming thiocarbamoyl compounds 8 a,b, which undergo heating with three types of α‐halogenated reagents to afford the corresponding substitutedthiophene‐3‐carboxamides 9 a,b. Condensation of keteneN,S‐acetals 10 a,b with hydrazines furnished the thiophene‐pyrazole‐4‐carboxamide hybrids 11 a,b, while condensation with urea and/or thiourea afforded the corresponding thiophene‐pyrimidine‐5‐carboxamides 12 a,b. The recently synthesized thiophene compounds were characterized there in vitro anticancer properties against HepG2 (hepatocellular carcinoma) and MDA‐MB‐231 (breast cancer) were evaluated. Molecular docking was also performed to predict the binding modes of synthesized derivatives with the good anticancer results designed as potential inhibitors for a specific target.

Novel carbazolyl-thiazolyl-chromone and carbazolyl-thiazolyl-pyrazole hybrids: synthesis, cytotoxicity evaluation and molecular docking studies.

A simple synthetic method was performed to design a novel series of polycyclic systems consisting of carbazole-thiazolidinone-chromone hybrids 4a-e and carbazole-thiazolidinone-pyrazole hybrids 5a-e in excellent yields. The methodology depended on the one-pot four-component reaction of 3-amino-9-ethylcarbazole, substituted isothiocyanates, ethyl bromoacetate and 6-methyl-3-formylchromone in ethanol under ultrasound waves at 50 °C to give the carbazole-thiazolidinone-chromone hybrids 4a-e. The latter isolated products were treated with hydrazine hydrate in ethanol under ultrasound waves at 50 °C affording the corresponding carbazole-thiazolidinone-pyrazole hybrids 5a-e. Spectral and analytical data confirmed the structures of all the synthesized compounds. The target compounds were screened for their in vitro anticancer activities against HCT116, PC3 and HepG2 cancer cell lines using the standard SRB method. Fortunately, both compounds 5dand5e were the most active against all cancer cell lines compared with doxorubicin and can be promising anticancer agents. Both bioactive products 5band5e were studied by the molecular docking to see how they bind with VEGFR-2 receptor. The results indicated that those compounds exhibited high affinities towards VEGFR-2 and established remarkably similar interactions to those of the powerful VEGFR-2-KDR.

Synthesis, crystal structure, spectroscopic characterization, DFT calculations, Hirshfeld surface analysis, molecular docking, and molecular dynamics simulation investigations of novel pyrazolopyranopyrimidine derivatives

A series of new pyrazolopyranopyrimidine derivatives (3-9) were synthesized from 5-amino-2,4-dihydro-3-methyl-4-phenylpyrano-[2,3-c]pyrazole-5-carbonitrile (2) by multicomponent reactions (MCR) involving malononitrile, benzaldehyde, and pyrazolone under refluxing ethanol in the presence of piperidine. Compound (2) was then converted to 2-acetylpyrazolopyranopyrimidine (3) through a reaction with acetic anhydride. The deprotection of 3 using ammonium hydroxide in ethanol, leads to 4. Subsequent chlorination of 4 by phosphorus oxychloride affords 5 which was alkylated using methyl iodide and ethyl bromoacetate in DMF, leading to regioisomers 6-9. The products were characterized by spectroscopic techniques (1H and 13C NMR) and confirmed by single crystal X-ray diffraction (XRD) studies for 2, 5, 6, and 9. Moreover, the geometrical parameters, molecular orbital calculations, and spectral data of 2, 5, 6, and 9 were compared by DFT at the B3LYP/6-311G(d,p) level of theory. There is good agreement between the calculated results and the experimental data. The intermolecular contacts for 2, 5, 6, and 9 were studied by Hirshfeld surface analysis. In addition, the molecular docky study was conducted to investigate the binding patterns of 2, 5, 6, and 9 within the binding site of cyclin-dependent kinase 2 (CDK2) and penicillin-binding protein 1 A. After the docking process, molecular dynamics (MD) simulations for 100 ns were performed on CDK2 and PBP 1 A proteins in the complex with 5. Communicated by Ramaswamy H. Sarma

Facile Synthesis, Spectroscopic and Nonlinear Optical Insights of Hydrazinyl-Based Functional Materials: Experimental and DFT Approach

A series of hydrazinyl thiazol-4-one based scaffolds (EBHT1-ETHT5) had been prepared through condensation process of substituted thiosemicarbazone with ethyl bromoacetate and sodium acetate. The structure confirmation of formed compounds was done through several spectroscopic methods. Beside synthesis, quantum chemical investigations were executed at MPW1PW91/6-311G(d,p) functional to explore nonlinearity of EBHT1-ETHT5. At first, the structures of prepared chromophores were optimized to get true minima geometries. These optimized geometries were further utilized to carry out the natural bond orbitals (NBO), transition density matrix (TDMx), UV-Vis analysis, density of states (DOS), and nonlinear optic (NLO) characteristics. A minimum Egap (4.433 eV) was achieved in EBHT1 with wider absorption spectrum (λ max= 339 nm) than that of other yielded compounds. A significant charge transference is seen with in molecules through DOS and TDM findings. The GRPs findings explored that all the afore-said chromophores had higher value of global hardness (η = 4.433–4.657 eV) along with lower softness (σ = 0.432–0.277 eV). Significant NLO results were obtained for prepared chromophores as compared to reference urea chromophore. These organic chromophores can be considered as potential candidates in NLO-based applications.

Lower rim thiacalixarenes derivatives incorporating multiple coordinating carbonyl groups: Synthesis, characterization, ion-responsive ability and DFT computational analysis

Three novel tetra substituted p‑tert-butylthiacalix[4]arene derivatives (3, 4, and 5) with five coordinating carbonyl groups at the lower rims were synthesized. Accordingly, diethyl tetra-t‑butyl‑trihydroxy-tetrathia-tetrabenzenacyclooctaphanyl)oxy)malonate react with ethyl bromoacetate, phenacyl bromide and 2‑chloro-N-(p-tolyl)acetamide, to produce new p‑tert-butylthiacalix[4]arenes in of 60, 90, and 80% yields, respectively. The molecular structures of the products were verified using FT-IR, 1H NMR, and 13C NMR spectroscopy. Metal ions such as Na+, K+, Cs+, Hg2+, Cd2+, Pb2+, Ni2+, Co2+, Cu2+, and Ag+ are easily chelated by the new thiacalixarene derivatives using liquid-liquid extraction technique. These compounds surprisingly show high efficiency in liquid-liquid extraction of alkali, heavy, and transition metal ions. Uptake efficiencies of 71.00% (for Co(II)), 46.00% (for Cu(II), and 15.00% (for Hg(II)) were attained by thiacalixarene 3, 4, and 5. These derivatives were subjected to DFT-based computational analysis with the aim of increasing the efficiency with which thiacalixarene (as a nucleophilic) interacts with the metal ion (3, 4, and 5 in the role of electrophile).

Design and Synthesis of Pyridine and Thiazole Derivatives as Eco-friendly Insecticidal to Control Olive Pests.

Treatment of p-tosyloxybenzaldehyde (1) with ethyl cyanoacetate afforded ethyl 2-cyano-3-(4-{[(4-methylphenyl)sulfonyl]oxy}phenyl)acrylate (2) which reacted with some active methylene derivatives under microwave irradiation in presence of ammonium acetate yielded pyridine derivatives 3-7. On the other hand, when treatment of compound 1 with thiosemicarbazide gave 4-tosyloxybenzylidenethiosemicarbazone (8), which allowed to react with some active methylene compounds, such as: ethyl bromoacetate, chloroacetonitrile or phenacyl bromide derivatives gave thiazole derivatives 9-13. The structure of all products were confirmed by elemental and spectroscopic analyses such as IR, 1 H-NMR, 13 CNMR and mass spectra. The advanced of this method are short reaction time (3-7 min), excellent yield, pure products, and low-cost processing. In the final category, the toxicological characteristics of all compounds were tested towards Saissetia oleae (Olivier, 1791) (Hemiptera: Coccidae). With respect to the LC50 values. It has been found that compound 3 possesses the highest insecticidal bioefficacy compared with other products, with values of 0.502 and 1.009 ppm, for nymphs and adults female, respectively. This study paves the way towards discovering new materials for potential use as insecticidal active agents.

DNA-Compatible Synthesis of Thiazolidione Derivatives via Three-Component Annulation and Knoevenagel Condensation.

Thiazolidione, conferring drug-like properties, is an important heterocycle that widely exists in medicinally relevant molecules. In this work, by efficiently assembling various DNA-tagged primary amines, abundant aryl isothiocyanates, and ethyl bromoacetate, we present a DNA-compatible three-component annulation to generate a 2-iminothiazolidin-4-one scaffold, which was further decorated via Knoevenagel condensation by employing (hetero)aryl and alkyl aldehydes. These thiazolidione derivatives should find broad use in focused DNA-encoded library construction.

A DDQ-mediated ring-opening and aromatization cascade of a tetrahydrocarbazole-fused tetrahydrofuran for the synthesis of olivacine

It is introduced that an N-MOM-tetrahydrocarbazole-fused tetrahydrofuran is a new intermediate for the synthesis of olivacine. Upon treatment with DDQ in a mixture of H2O-THF at 80 °C, it undergoes ring-opening, MOM-removal and aromatization in one pot to yield 1-methyl-carbazole-2-ethanol, an already known precursor for olivacine. Besides, several common transformations, such as α-alklylation of N-MOM-protected tetrahydrocarbazole-1-one with ethyl bromoacetate and reduction of a lactone to tetrahydrofuran with Red-Al, have been made good use.

Design, Synthesis, and Biological Evaluation of 1,2,4-Triazole Derivatives as Potential Antimicrobial Agents

In this study, we aimed to develop new biologically active compounds with antibacterial properties. 4-amino-5-methyl-2H-1,2,4-triazol-3(4H)-one (1) was converted to the corresponding Schiff bases (2) with the reaction with a 4-anis aldehyde. Acetic acid ethyl esters containing [1,2,4] triazole ring (3) were synthesized by the condensation of compounds (2) with ethyl bromoacetate in basic media. The reaction of compounds (3) with hydrazine hydrate led to the formation of acid hydrazides (4). The reaction of hydrazide (4) with phenyl isothio - and phenyl isocyanate produced the corresponding carbothioamide (5a) and carboxamide (5b). The basic treatment of carbothioamide (5a) and. carboxamide (5b) produced 1,2,4-triazole (6a, 6b) compounds, respectively. The reactions of ( (6b) with norfloxacin and ciprofloxacin in the presence of formaldehyde afforded the corresponding Mannich bases( 7a, 7b). The structural assignments of the new compounds were based on elemental analysis and spectral (IR, 1H-NMR, and 13C-NMR) data. All newly synthesized compounds were screened for their antimicrobial activity. The in vitro antimicrobial activities of the compounds were evaluated against pathogenic microorganisms, and compounds 7a and 7b were found the most effective antimicrobial activity.

14- and 17-Membered Macrocycles Containing Amide, Amino, and Carbamate Groups in The Monocyclic Skeleton: An Accidental Byproduct Obtained from a Residue after Separation.

A 14-membered cyclic compound (3) containing amide, amino, and carbamate groups, which was serendipitously obtained in the oily residue after the separation of 4-benzyl-1,4,7,10-tetraazacyldododecane-2,6-dione (2a) and 4,16-dibenzyl-1,4,7,10,13,16,19,22-octaazacyclo-tetracosane-2,6,14,18-tetraone (2b), is reported. The structure of 3 is formally a CO2 insertion between positions 3 and 4 of the 12-membered ring in 2a. The CO2 insertion was confirmed in the synthesis of diethyl 2,2'-(benzylazanediyl)diacetate (1) by the reaction of benzylamine with ethyl bromoacetate using K2CO3 as the base. In addition, the selective synthesis of 3 and ethyl N-benzyl-N-((2-ethoxy-2-oxoethoxy)carbonyl)glycinate (5) and their kinetic behavior are reported. The reaction of 5 with triethylenetetramine afforded a 17-membered macrocycle (7), which was obtained in an 18% yield. Compounds 6 and 8 were prepared from 3 and 7 by introducing benzyl groups to improve their solubility in organic solvents. Titration experiments using 1H NMR showed that both 6 and 8 exhibit Li+ selectivity.

Synthesis of N-Mannich bases from 5-((4-methylpiperazin-1-yl)methyl)-1,3,4-oxadiazole-2-thiol

Methyl (4-methylpiperazin-1-yl)acetate (2) were synthesized by the condensation of compound (1) with ethyl bromoacetate in basic media. aThe synthesis of acid hydrazide derivatives (3) was brought about as a result of the reaction between a compound (2) and hydrazine hydrate. In the absence of basic conditions, the reaction of 2-(4-methylpiperazin-1-yl)acetohydrazide (3) with carbon disulfide resulted in the formation of 5-((4-methylpiperazin-1-yl)methyl)-1,3,4-oxadiazole-2-thiol (4). aThe reactions of (4) with different primary and secondary amines in the presence of formaldehyde led to the formation of the corresponding Mannich bases (5a-f).

Synthesis, crystal structure and evaluation of anticancer activities of some novel heterocyclic compounds based on thymol

A series of novel 1,3,4-thiadiazole, 1,3-thiazole and 1,3-thiazolidin-4-one derivatives bearing thymol were synthesized via cyclization of the corresponding thiosemicarbazones with acetic anhydride, ethyl bromoacetate, dimethyl acetylene dicarboxylate and phenacyl bromides. The structures of the newly synthesized compounds have been confirmed by IR, 1H NMR, 13C NMR, HRMS and single crystal X-ray diffraction analyses. All new thiosemicarbazones and their heterocyclic derivatives were evaluated for their in vitro cytotoxicity against four selected human cancer cell lines, namely, breast adenocarcinoma (MCF-7, MDA-MB- 231), lung carcinoma (A-549) and fibrosarcoma (HT-1080) cell line and compared with reference drug doxorubicine. The data illustrate that most target compounds show moderate to high cytotoxicity activities against the four human cancer cell lines. Especially, thiosemicarbazones 4b showed significant cytotoxicity on HT-1080 and A-549 cancer cell line with an IC50 values of 7.10 ± 0.32 and 14.40 ± 0.36 µM, respectively. Notably, induction of apoptosis by the compound 4b on HT-1080 and A-549 cells was evaluated using different staining techniques such as annexin V-FITC/PI. Moreover, flow-cytometric analysis also revealed that compound 4b caused arrest at the G2/M phase of the cell cycle and caspase-dependent apoptosis in HT-1080 and A-549 cells.

Enantioselective Synthesis of 2,3-Dihydrofurans Using the Catalyst of Camphor/Pinene-Based Bypiridine

This research describes the synthesis of two kinds of chiral ligand and their application in the cyclization of 2,3-dihydrofuran. They are camphor-based bipyridine and pinene-based bipyridine. These ligands were prepared followed the known procedure, and they were used for the enantioselective preparation of 2,3-dihydrofuran in the present of enone and ethyl bromoacetate. Ligand that gives the highest enantioselectivity value is pinene bipyridine-salt with 56% ee for cis isomer (86% yield) while 30% ee is obtained for trans isomer of 2,3-dihydrofuran (1/3).

One‐pot multicomponent designing of novel 2‐imino‐4‐arylidene‐1,3‐thiazolidin‐4‐one

AbstractAn unprecedented series of 2‐imino‐1,3‐thiazolidin‐4‐ones were designed by straightforward and dynamic technique via one‐pot three‐component reaction of isothiocyanatobenzene, primary amines, ethyl bromoacetate and/or phenacylbromide. Furthermore, we found that the reaction between 2‐imino‐1,3‐thiazolidin‐4‐one and arylidenemalononitrile using of C2H5ONa as catalyst gave the corresponding 3‐(2‐phenylethyl)‐5‐(4‐arylidene)‐2‐(phenyl imino)‐1,3‐thia‐zolidin‐4‐one instead of 5‐amino‐7‐aryl‐3‐(2‐phenylethyl)‐2‐(phenylimino)‐3,7‐dihydro‐2H‐6‐carbonitrile. The identical molecules were designed through other routes via the reaction of 2‐imino‐1,3‐thiazolidin‐4‐one with the corresponding aryl carbaldehyde.

Synthesis and Identification of New N,N-Disubstituted Thiourea, and Thiazolidinone Scaffolds Based on Quinolone Moiety as Urease Inhibitor.

Synthesis of thiazolidinone based on quinolone moiety was established starting from 4-hydroxyquinol-2-ones. The strategy started with the reaction of ethyl bromoacetate with 4-hydroxyquinoline to give the corresponding ethyl oxoquinolinyl acetates, which reacted with hydrazine hydrate to afford the hydrazide derivatives. Subsequently, hydrazides reacted with isothiocyanate derivatives to give the corresponding N,N-disubstituted thioureas. Finally, on subjecting the N,N-disubstituted thioureas with dialkyl acetylenedicarboxylates, cyclization occurred, and thiazolidinone derivatives were obtained in good yields. The two series based on quinolone moiety, one containing N,N-disubstituted thioureas and the other containing thiazolidinone functionalities, were screened for their in vitro urease inhibition properties using thiourea and acetohydroxamic acid as standard inhibitors. The inhibition values of the synthesized thioureas and thiazolidinones exhibited moderate to good inhibitory effects. The structure−activity relationship revealed that N-methyl quinolonyl moiety exhibited a superior effect, since it was proved to be the most potent inhibitor in the present series achieving (IC50 = 1.83 ± 0.79 µM). The previous compound exhibited relatively much greater activity, being approximately 12-fold more potent than thiourea and acetohydroxamic acid as references. Molecular docking analysis showed a good protein−ligand interaction profile against the urease target (PDBID: 4UBP), emphasizing the electronic and geometric effect of N,N-disubstituted thiourea.

Synthesis and Anticancer Evaluation of New Thiazole and Thiadiazole Derivatives Bearing Acetanilide Moiety.

New thiazole and thiadiazole derivatives bound to the acetanilide moiety were synthesized and evaluated for their cytotoxic activity. The precursor N-(4-acetamidophenyl)-N'-phenylthiourea (2) was cyclocondensed with ethyl bromoacetate to afford a mixture of the two isomers, 2-(4-acetamidophenylimino)-3-phenylthiazolidin-4-one (3a, 23%) and 3-(4-acetamidophenyl)-2-phenyliminothiazolidin-4-one (3b, 71%). The Knoevenagel reaction of 3b with various aromatic aldehydes afforded 5-arylidene-2-phenyliminothiazolidin-4-one derivatives 5a-5e. Intramolecular cyclization of thiourea scaffold 2 with chloroacetone and/or phenacyl chloride gave the conforming thiazole derivatives 6a and 6b. A new series of thiadiazole derivatives 9a-9c and 11a-11c was synthesized by the reaction of N-(4-acetamidophenyl)-N'-phenylthiourea (2) with selected derivatives of hydrazonoyl halide in ethanol and triethylamine. The structures of the synthesized thiazole and thiadiazole compounds were elucidated by their compatible spectral data. The cytotoxic activity of the synthesized thiazole and thiadiazole derivatives was screened against four human cancer cell lines and showed promising results. Thiazolidin-4-one compound 5d showed the strongest cytotoxic effects on hepatocellular carcinoma (IC50 = 8.80 ± 0.31 μg/mL), mammary gland breast cancer (IC50 = 7.22 ± 0.65 μg/mL) and colorectal carcinoma (IC50 = 9.35 ± 0.61 μg/mL) cell lines.

Imidazole-Based Bronsted Acidic Surfactant: A Novel Regioselective Catalytic System for Making of 2-Aryl-1,2-Dihydrothiazolo[3,2-b][1, 2, 4]Triazol-6(5H)-Ones

We have synthesized a novel bronsted acidic surfactant, 3-methyl-1-sulfonic acid imidazolium dioctyl sulfosuccinate [MSIM]+ [DOSS]−. We explored catalytic activity of [MSIM]+ [DOSS]− for regioselective synthesis of novel class of thiazolotriazolones from the reaction of aldehydes/ketones, thiosemicarbazide and ethylbromo acetate in aqueous medium at room temperature. The regio-selectivity was confirmed by DFT and IR frequency calculations. The present methodology offers a feasible approach for swift access to collection of extremely pure products with wide substrate scope having several advantages such as excellent yields, short reaction time, easy work-up procedure for isolation of product and use of surfactant as eco-friendly catalyst, use of water as an universal solvent and novelty in synthesis of surfactant [MSIM]+ [DOSS]− as well as investigation of regioselective synthesis of novel class of thiazolotriazolones.