Synthesis Of Novel Benzo Research Articles

Environmentally Benign Copper Triflate‐Mediated Multicomponent One‐Pot Synthesis of Novel Benzo[g]chromenes Possess Potent Anticancer Activity

AbstractAn efficient multi‐component one‐pot synthesis of highly functionalized 5,10‐dihydro‐4H‐benzo[g]chromenes‐3‐caronitrile derivatives from 2‐hydroxy‐1,4‐naphthoquinone, aromatic aldehyde and malonitrile in the presence of Cu(OTf)2 catalyst and eco friendly polyethylene glycol solvent was carried out under ultrasonication. The reaction was completed within 10 minutes and resulted in good yield. The synthesized compounds were tested for their in‐vitro anticancer activity against cervical cancer cell line (HeLa). Nine out of ten compounds showed potent antitumor activity better than that of doxorubicin. 2‐Amino‐4‐(3‐methoxy‐2‐hydroxy)‐5,10‐dioxo‐5,10‐dihydro‐4H‐benzo[g]chromene‐3‐carbonitrile displayed highest activity among the test compounds and doxorubicin with IC50 equal to 1.27 μM.

Barium aluminate nano-powders efficient catalyst for the synthesis of novel benzo[b]thiophene, thieno[2,3-c]thiopyran and thieno[2,3-c]pyridine derivatives

GRAPHICAL ABSTRACT

Barium aluminate nano-powders efficient catalyst for the synthesis of novel benzo[b]thiophene, thieno[2,3-c]thiopyran and thieno[2,3-c]pyridine derivatives

Uniform nanopowders of barium aluminate (BaAl 2 O 4 ) can be synthesized by a facile solution reaction at room temperature using barium and aluminum salts and 2-aminoethanol as a precipitating agent. The as-prepared sample showed a good reactivity in the synthesis of benzo[b]thiophene, thieno[2,3-c]thiopyran and thieno[2,3-c]pyridine derivatives. Comparatively the method is efficient and eco-friendly, and finally, a range of compounds with variable functionalities in excellent yield can be achieved.

Caffeine catalyzed green synthesis of novel benzo[a][1,3]oxazino[6,5-c]phenazines via a one-pot multi-component sequential protocol in a basic ionic liquid

Caffeine was applied as a green and natural catalyst for the one-pot, four-component sequential condensation between 2-hydroxy-1,4-naphthoquinone, aromatic 1,2-diamines, ammonium thiocyanate and acid chlorides in the presence of a basic ionic liquid (1-butyl-3-methylimidazolium hydroxide) to afford the corresponding benzo[a][1,3]oxazino[6,5-c]phenazine derivatives. In this one-pot transformation, five bonds and two new rings are efficiently formed. This protocol has the advantages of operational simplicity, high yields, easy workup, avoidance of hazardous or toxic catalysts and organic solvents and high chemo- and regioselectivities.

A rapid, efficient, and green synthesis of benzo[$a$]chromeno[2,3-$c$]phenazine derivatives via microwave assistance and DABCO~catalyzed a novel domino cyclization

An efficient, convenient, and environmentally benign procedure for the synthesis of novel benzo[$a$]chromeno[2,3-$c$]phenazine derivatives has been developed by domino four-component condensation reaction between 2-hydroxynaphtha- lene-1,4-dione, $o-$phenylenediamine, aromatic aldehydes, and naphthols or phenol in the presence of a catalytic amount of DABCO as an expedient, ecofriendly, and reusable base catalyst under microwave irradiation in EtOH/H$_{2}$O (1:1). This green process produces biologically and pharmacologically significant heterocycles in a single one-pot operation and offers considerable advantages such as operational simplicity, short reaction time, high yields, reusability of the catalyst, absence of any tedious workup or purification, and avoidance of hazardous reagents/solvents.

Efficient synthesis of novel benzo [f]imidazo[1,2-d][1,4]oxazepine-5(6H)-one derivatives

A convenient and efficient method is described for the synthesis of novel tricyclic scaffolds incorporating an imidazole ring and medium-sized benzoxazepine ring, via the reaction of 1,2-diketons, 2-formyl phenoxy acetic acids and ammonium acetate in acetic acid under reflux conditions, and then the addition of thionyl chloride to produce lactam in the absence of a catalyst.

ChemInform Abstract: Synthesis of Novel Benzo[b]pyrimido[4′,5′:5,4]thieno[2,3‐e][1,6]naphthyridine‐8‐ones via Pictet—Spengler Cyclization.

Abstract An efficient method for the synthesis of novel benzo[b]pyrimido[4′,5′:5,4]thieno[2,3e]-[1,6]naphthyridine-8-one derivatives via Pictet–Spengler cyclization is reported. The reaction of 4-(3-aminopyrimido[4,5-d]thieno-2-yl)quinoline-2-ones, which could be obtained from Thorpe–Ziegler isomerization of 4-bromomethylquinoline-2-ones and 5-cyano-1,6-dihydro-4-methyl-2-phenyl-6-thioxopyrimidine, with aromatic aldehydes in the presence of BF3·OEt2 gives pyrimidothieno[1,6]naphthyridines in good yields.

Solvent‐Free Pot‐, Atom‐ and Step‐Economic Synthesis of Novel Benzo[d]thiazole‐[1,3]‐thiazine Hybrids in a One‐Pot Reaction

AbstractThe first catalyst‐ and solvent‐free synthesis of novel benzo[d]thiazole‐[1,3]‐thiazine hybrids from benzo[d]thiazol‐2‐amines, isothiocyanates and dialkyl acetylenedicarboxylates with no more than 30 min of microwave irradiation is described. Moreover, the proposed strategy involves neither tedious workup nor column purification steps. This approach provides a diversity‐oriented route for the rapid assembly of benzo[d]thiazole‐[1,3]‐thiazine frameworks. Furthermore, the methodology has excellent green credentials, scoring well in a number of green metrics, hence showing this approach to be an ideal green and sustainable process.

Design and synthesis of novel benzo[d]oxazol-2(3H)-one derivatives bearing 7-substituted-4-enthoxyquinoline moieties as c-Met kinase inhibitors

Analysis of the results of studies of docking 1 and 7a with c-Met kinase led to the identification of benzo[d]oxazol-2(3H)-one-quinolone derivatives as potential inhibitors of this enzyme. A molecular hybrid strategy, using a 4-ethoxy-7-substituted-quinoline core and a benzo[d]oxazol-2(3H)-one scaffold, was employed to design members of this family for study as inhibitors of the kinase and proliferation of EBC-1 cells. Most of the substances were found to display good to excellent c-Met kinase inhibitory activities. The results of a structure–activity relationship (SAR) study led to the discovery of benzo[d]oxazol-2(3H)-one-quinolone 13, which has IC50 values of 1 nM against c-Met kinase and 5 nM against proliferation of the EBC-1 cell line.

Synthesis of novel benzo[ b ]pyrimido[4′,5′:5,4]thieno[2,3-e][1,6]naphthyridine-8-ones via Pictet–Spengler cyclization

Abstract An efficient method for the synthesis of novel benzo[b]pyrimido[4′,5′:5,4]thieno[2,3e]-[1,6]naphthyridine-8-one derivatives via Pictet–Spengler cyclization is reported. The reaction of 4-(3-aminopyrimido[4,5-d]thieno-2-yl)quinoline-2-ones, which could be obtained from Thorpe–Ziegler isomerization of 4-bromomethylquinoline-2-ones and 5-cyano-1,6-dihydro-4-methyl-2-phenyl-6-thioxopyrimidine, with aromatic aldehydes in the presence of BF3·OEt2 gives pyrimidothieno[1,6]naphthyridines in good yields.

An efficient synthesis of novel benzo[b]pyrido[3′,2′:4,5]thieno[2,3-e][1,6]naphthy-ridine-8-ones

Abstract An efficient method for the synthesis of novel benzo[b]pyrido[3′,2′:4,5] thieno[2,3-e][1,6] naphthyridine-8-one derivatives has been developed using a Pictet–Spengler reaction between 4-(3-aminothieno[2,3-b]pyridin-2-yl)quinoline-2-ones, which could be obtained from the alkylation of 4-bromomethylquinoline-2-ones with 3-cyanopyridine-2-thione followed by a Thorpe–Ziegler isomerization, and aromatic aldehydes under p -TsOH as catalysis in good yields.

3-Azidothieno[2,3-b]pyridine Thermolysis as a Route to Novel peri-Annelated Heterocyclic Derivatives – Benzo(furo)thieno[2,3,4-ij]-2,7-naphthyridines

Synthesis of novel benzo(furo)thieno[2,3,4- ij ]-2,7-naphthyridines based on alkyl(aryl) 3-azido-4-aryl(furyl)thieno[2,3- b ]pyridine-2-carboxylate thermolysis is elaborated. The structures of the synthesized materials were assigned by their NMR, IR, and MS analysis.

3-Azidothieno[2,3-b]pyridine Thermolysis as a Route to Novel peri-Annelated Heterocyclic Derivatives – Benzo(furo)thieno[2,3,4-ij]-2,7-naphthyridines

Synthesis of novel benzo(furo)thieno[2,3,4-<i>ij</i>]-2,7-naphthyridines based on alkyl(aryl) 3-azido-4-aryl(furyl)thieno[2,3-<i>b</i>]pyridine-2-carboxylate thermolysis is elaborated. The structures of the synthesized materials were assigned by their NMR, IR, and MS analysis.

ChemInform Abstract: NHC—Gold(I) Catalyzed [4 + 2] Cycloaddition—Acyclic Addition of Dialkyl Substituted Propargylic Esters with 1,3‐Diphenylisobenzofuran: Synthesis of Novel Benzo[c]fluorenols and Substituted Dienes.

AbstractA new type of cycloaddition involving propargylic esters is discovered.

An efficient catalyst-free synthesis of novel benzo[a][1,3]oxazino[6,5-c]phenazine derivatives via one pot four-component domino protocol in water

A catalyst-free multicomponent reaction (MCR) capable of affording a wide range of novel benzo[a][1,3]oxazino[6,5-c]phenazine derivatives via one pot two-step domino protocol, in water is reported. Catalyst-free conditions along with green solvent system make the process ecofriendly as well as economical. Simple reaction conditions, easy work-up isolation, and purification of products are the significant advantages of the present protocol.

Novel synthesis of benzo[b]carbazoles

A new method was adopted for the synthesis of benzo[b]carbazoles by Claisen condensation followed by Fischer indole cyclization. Newly synthesized benzo[b]carbazoles were treated with ethanol amine in the presence of polyphosphoric acid which leads to the formation of pyrazino carbazoles. All the synthesized compounds were characterized by all spectral means.

ChemInform Abstract: Synthesis of Novel Benzo[4,5]thiazolo[1,2‐a]pyrimidine‐3‐carboxylate Derivatives and Biological Evaluation as Potential Anticancer Agents.

AbstractTwo series of novel benzothiazolopyrimidine carboxamide derivatives (VI) and (VII) are synthesized and evaluated for their cytotoxicity against some human cancer cell lines.

Cu-Catalyzed Synthesis of Novel Benzo[e]pyrazolo[1,5-c][1,3]-thiazine Derivatives

基于底物设计的概念,建立了一种以1-（2-溴芳基）-3-乙氧基-3-（取代胺基）-2-丙烯-1-酮（1）为原料,经由5-（2-溴芳基）-3-取代胺基-1H-吡唑（2）和异硫氰酸酯（3）在溴化亚铜/邻菲罗啉催化下高化学选择性地合成苯并[e]吡唑并[1,5-c][1,3]噻嗪类衍生物的新方法。该方法操作简单、反应条件温和且收率高。

NHC–gold(i) catalysed [4 + 2] cycloaddition–acyclic addition of dialkyl substituted propargylic esters with 1,3-diphenylisobenzofuran: synthesis of novel benzo[c]fluorenols and substituted dienes

A new class of benzofluorenols is generated via a novel gold carbene complex [IPrAuCl/AgSbF6] catalysed cycloaddition of propargylic esters with 1,3-diphenylisobenzofuran.

Synthesis and in vitro anti-inflammatory activity of novel benzo[d] imidazolyl dihydrospiro[indoline-3,1′-isoindole]-2,4′,7′-triones

Synthesis of novel benzo[d]imidazolyldihydrospiro[indoline-3,1′-isoindole]-2,4′,7′-triones has been described. The key intermediate 2-[(2-sulfanyl-1H-benzo[d]imidazol-5-yl)amino]acetic acid is obtained by reacting 5-amino-2-mercapto benzimidazole and chloroacetic acid. The three-component reaction of 2-[(2-sulfanyl-1H-benzo[d]imidazol-5-yl)amino]acetic acid with isatin and 1,4-benzoquinone in the presence of 10 mol% of L-proline at ambient temperature afforded 2′-(2-mercapto-1H-benzo [d] imidazol-5-yl)-3′,3a′-dihydrospiro[indoline-3,1′-isoindole]-2,4′,7′(2′H,7a′H)-triones. All the synthesized compounds were evaluated for in vitro anti-inflammatory activity.