Phenoxyacetyl Chloride Research Articles

Studies on Fused β-Lactams: Synthesis of 1-Aza Analogs of Cephem

Abstract Annelation of 2-methylthio-3,4-dihydropyrimidine (3) with two moles of phenoxyacetyl chloride in presence of triethylamine did not yield the expected β-lactam (6) and instead the N-acylated compound 5a was obtained. Various N-acylated pyrimidines 5a–d also failed to yield any β-lactam. However, β-lactam ring has been conveniently grafted on to 2-methylthio-3,6-dihydropyrimidines 9a–d, 12 by annelating them with in situ prepared aryloxyketenes to furnish novel 1-aza analogs of cephem 10a–e and 13.

Preparation, Characterization and Stereochemistry of Mixed Anhydrides of O-Alkylbenzohydroximic Acid

A number of stable isoimides have been prepared by acylation and sulfonylation of O-benzylbenzohydroxamic acid and O-butylbenzohydroxamic acid by anisoyl chloride, benzoyl chloride, phenoxyacetyl chloride, p-toluenesulfonyl chloride, benzenesulfonyl chloride and p-nitrobenzenesulfonyl chloride in the presence of pyridine. Spectral investigations indicate that the products have the mixed anhydride structure with (Z)-configuration. Corresponding (E)-isomers and isomeric N-acetylated products if formed, could not be isolated. An attempt has been made to study 1,3-rearrangement of the mixed anhydrides by thermal method.

ChemInform Abstract: A Mild Four‐Carbon Homologation of 4‐Formylazetidinones.

AbstractThe azetidinones (III), prepared from the acid chloride (I) and the imines (II) via ketene cycloaddition reaction, are N‐deprotected and reprotected with phenoxyacetyl chloride (IV) to give the amino derivatives (V).

ChemInform Abstract: Synthesis and Antibacterial Activity of Some New 2‐Aryloxymethyl 3‐Substituted Quinazolin‐4(3H)‐ones.

AbstractCyclocondensation of anthranilic acid (I) with the phenoxyacetyl chlorides (II) leads to the formation of the benzoxazin‐4‐ones (III) which form the quinazolin‐4(3H)‐ones (V) upon ring closure with the aniline derivatives (IV) in boiling pyridine.

On Triazoles. XIII. The reaction of 5‐benzalimino‐1,2,4‐triazoles with substituted acetyl chlorides

AbstractThe reaction of Schiff bases prepared from 1‐ and 2‐substituted‐5‐amino‐1,2,4‐triazoles with phenoxyacetyl chlorides in the presence of triethylamine and a mixture of phosphorus oxychloride and dichloroacetic acid in dimethylformamide to yield β‐lactam 4, a dihydro‐1,2,4‐triazolo[4,3‐a]pyrimidine‐5(1H)‐one 5, a 1,2,4‐triazolo[1,5‐a]pyrimidin‐5(3H)‐one 9 and the corresponding 1,2,4‐triazolo[4,3‐a]pyrimidine‐5(1H)‐one 10 derivatives was studied.

1H NMR spectra of some juvabione analogues

A number of aromatic aza-analogues of juvabione and dehydrojuvabione have been synthetized by treatment of substituted benzylamine with 3-methylbutanoyl chloride and 3-methyl-2-butenoyl chloride. Reaction of substituted phenoxyacetyl chlorides with isopropylamine and 2-propanol gives other series of aromatic juvabione analogues. The 1H NMR spectra of some analogues are discussed.

Synthesis of some new 2-(phenoxyacetylthio)-3-aryl-6-bromo- or -6,8-dibromoquinazoline-4(3H)-ones as possible AChE inhibitors.

AbstractSixteen new 2‐(phenoxyacetylthio)‐3‐aryl‐6‐bromo‐ or ‐6,8‐dibromoquinazolones were synthesized by condensation of various phenoxyacetyl chlorides with mercaptoquinazolones. Their inhibitory properties towards choline esterase and their bactericidal activities were studied in vitro. Nine of the compounds exhibited (>50%) choline esterase inhibition, whereas the antibacterial screening showed moderate results.

ChemInform Abstract: SYNTHESIS OF (CHLOROMETHOXY)BENZENES BY CATALYTIC DECARBONYLATION OF PHENOXYACETYL CHLORIDES WITH CHLOROTRIS(TRIPHENYLPHOSPHINE)RHODIUM(I)

Chemischer InformationsdienstVolume 13, Issue 43 Isocyclic Compounds ChemInform Abstract: SYNTHESIS OF (CHLOROMETHOXY)BENZENES BY CATALYTIC DECARBONYLATION OF PHENOXYACETYL CHLORIDES WITH CHLOROTRIS(TRIPHENYLPHOSPHINE)RHODIUM(I) T. BENNECHE, T. BENNECHESearch for more papers by this authorK. UNDHEIM, K. UNDHEIMSearch for more papers by this author T. BENNECHE, T. BENNECHESearch for more papers by this authorK. UNDHEIM, K. UNDHEIMSearch for more papers by this author First published: October 26, 1982 https://doi.org/10.1002/chin.198243187Read the full textAboutPDF ToolsRequest permissionExport citationAdd to favoritesTrack citation ShareShare Give accessShare full text accessShare full-text accessPlease review our Terms and Conditions of Use and check box below to share full-text version of article.I have read and accept the Wiley Online Library Terms and Conditions of UseShareable LinkUse the link below to share a full-text version of this article with your friends and colleagues. Learn more.Copy URL Share a linkShare onFacebookTwitterLinkedInRedditWechat No abstract is available for this article. Volume13, Issue43October 26, 1982 RelatedInformation

A CONVENIENT SYNTHESIS OF 2-DEOXY-d- RIBOSE

Abstract Successive treatment of allyltin difluoroiodide, formed in situ by the oxidative addition of stannous fluoride to allyliodide, with 1,2-O-isopropylidene-d-glyceraldehyde and phenoxyacetyl chloride results in the predominant formation of erythro homoallylester, which is in turn converted into 2-deoxy-d-ribose.

Synthesis of novel fused β-lactams by intramolecular 1,3-dipolar cycloadditions. Part 2. (8S,8aR)-7,8-dihydro-7-oxo-8-phenoxyacetamido-8aH-azeto[1,2-a]-v-triazolo[3,4-c]pyrimidine-5-carboxylic acids

The penicillin-derived (3R,4R)-4-methylthio-3-triphenylmethylaminoazetidin-2-one (10) has been converted into (3S,4R)-4-azido-1-(1-t-butoxycarbonylbut-3-ynyl)-3-triphenylmethylaminoazetidin-2-one (15a), which provided t-butyl(8S,8aR)-4,5,7,8-tetrahydro-7-oxo-8-triphenylmethylamino-8aH-azeto[1,2-a]-v-triazolo-[3,4-c]pyrimidine-5-carboxylate (16a) when heated in refluxing toluene. Conversion of (16a) into t-butyl (8S,8aR)-7,8-dihydro-7-oxo-8-triphenylmethylamino-8aH-azeto[1,2-a]-v-triazolo[3,4-c]pyrimidine-5-carboxylate (14a) was then accomplished via an α-selenenylation, oxidation sequence. Removal of the amino-protecting group from (14a), followed by acylation with phenoxyacetyl chloride and de-esterification provided the desired (8S,8aR)-7,8-dihydro-7-oxo-8-phenoxyacetamido-8aH-azeto[1,2-a]-v-triazolo[3,4-c]pyrimidine-5-carboxylic acid (20).

ChemInform Abstract: A SYNTHESIS OF 7α‐METHOXYCEPHALOSPORINS THROUGH SELENENAMIDES

AbstractDie Arylselenenylaminocephemcarboxylate (III) ‐ zugänglich aus den 7β‐Aminocephemen (I) und dem Arylselenenylchlorid (II) ‐ werden mit aktiviertem MnO, zu den Selenenylirninen (IV) oxidiert, die mit Li‐methylat zu den 7a‐Methoxy‐Derivaten (V) umgesetzt werden; neben (Vb) entsteht überwiegend das Az‐Isomere ( 26% Ausb.).

Conversion of some monocyclic β-lactams into novel di-β-lactams

Monocyclic β-lactams (V & XI) carrying a carboxy function have been used to annelate the Schiff bases (II & X) using POCl 3 in the presence of triethylamine to obtain the di-β-lactams (VI & XII). Alternately, (VI) could also be prepared by annelation of the Schiff base (IX) derived from the α-amino-β-lactam (VIII), with phenoxyacetyl chloride.

Stereospecific synthesis of some polycyclic cis-β-lactams

Amides 1 on reaction with P 2S 5 in pyridine give thioamides 2 which on treatment with methyl iodide afford the corresponding 1-methylthio-3,4-dihydroisoquinolines 3. Annelation of these imines with phenoxyacetyl chloride in the presence of triethylamine furnish 6-methylthio-7-phenoxy-2',3' - dimethoxybenzo[ a]octem 4a and 6-methylthio-7-phenoxy-2,3-methylenedioxybenzo[a]octem 4b respectively. Desulphurisation of these β-methylthio-β-lactams with Raney nickel yield the novel polycyclic cis-β-lactams 5a and 5b.

A Synthesis of 7α-Methoxycephalosporins through Selenenamides

Abstract The o-nitrobenzeneselenenamides were oxidized with active manganese dioxide to give the irnines, which were converted to the 7α-methoxycephalosporins 3 by the reaction with lithium methoxide. The selenenamides 3 were acylated with phenoxyacetyl chloride to afford the desired cephamycin derivatives 4 via tertiary amide 5, which was not isolable. This methoxylation reaction was also carried out in penicillin series to give the desired 6α-methoxypenicillin 8 although the ring opening compound 9 was a major product. The difference between sulfenamides and selenenamides in their acylation reactions was discussed.

Transformations of 3-methyl-2-azafluorene involving the methyl and methylene groups

The condensation of 3-methyl-2-azafluorene with benzaldehyde at the methyl group, as a result of which the cis and trans forms of 3-styryl-2-azafluorene are formed, proceeds without catalysts. The subsequent condensation with benzaldehyde takes place in the presence of potassium ethoxide and leads to 3-styryl-9-benzylidene-2-azafluorene. Treatment of azafluorene with phenoxyacetyl chloride in the presence of triethylamine yielded 3-methyl-9-(α-hydroxy-β-phenoxyethylidene)-2-azafluorene. On the basis of the spectral data it was concluded that the latter exists in the form of a mixture of the enol form and the zwitterionic form. 3-Methyl-9-(γ-phenyl-α-cinnamoyloxyallylidene)-2-azafluorene was obtained by acylation of azafluorene with cinnamoyl chloride under the same conditions. The PMR and IR spectral data are presented.

Synthesis of 1,2,3‐thiadiazoles

AbstractSeveral methods were explored for preparing certain 4,5‐disubstituted‐1,2,3‐thiadiazoles. The reaction of phenoxyacetyl chlorides with diazoacetylamides yielded α‐diazo‐β‐ketoacetamides which were cyclized, with hydrogen sulfide and ammonium hydroxide, to 4‐carboxamido‐5‐phenoxymethyl‐1,2,3‐thiadiazoles. However, treatment of α‐diazo‐α‐benzoylacetamides with hydrogen sulfide and ammonium hydroxide yielded hydrazones rather than thiadiazoles. The reaction of α‐[(ethoxycarbonyl)hydrazono]benzenepropanoic acid (25) with thionyl chloride yielded 5‐phenyl‐1,2,3‐thiadiazole‐4‐carbocylic acid (26a), the corresponding acid chloride 26b, and 5‐(phenylmethyl)‐2H‐1,3,4‐oxadiazine‐2,6(3H)dione (27). The yields of 26a, 26b, and 27 were dependent on the reaction conditions employed. Oxadiazine 27 could also be converted to acid chloride 26b with thionyl chloride. Reduction of 1‐([5‐(4‐chlorophenoxy)methyl‐1,2,3‐thiadiazol‐4‐yl]‐carbonyl)piperidine (10b) with diborane yielded a boron complex which produced 1‐([5‐((4‐chlorophenoxy)methyl)‐1,2,3‐thiadiazol‐4‐yl]methyl)piperidine (31) upon recrystallization from ethanol.

ChemInform Abstract: PREPARATION AND PROPERTIES OF 5‐PHENYLPHENOXYMETHYLPENICILLIN

AbstractAus Azido‐acetylchlorid (I) erhält man in Gegenwart von Triäthylamin über das Keten mit den Thiazolinen (IIa)‐(IIc) die Addukte (III), die zu den Aminen (IV) reduziert werden.

Preparation and properties of 5-phenylphenoxymethylpenicillin.

Cycloaddition of azidoacetyl chloride to benzyl D-5,5-dimethyl-5-phenyl-2-thiazoline-4-carboxylate (1a) gave 5-phenyl-6alpha-azidopenicillanate (2a). By catalytic reduction of 2a and reaction with phenoxyacetyl chloride, 5-phenyl-6-epiphenoxymethylpenicillin benzyl ester (4a) was obtained. Oxidation of 4a gave the sulfoxide 6, which was isomerized in the presence of DBN. The sulfoxide 7 with the normal configuration could be isolated but deoxygenation of the sulfoxide was not successful. Isomerization of 4a with DBN, either with or without silylation of the side chain, gave a mixture from which 5-phenylphenoxymethylpenicillin benzyl ester (5) was isolated. Compound 5 was debenzylated to 5-phenylphenoxymethylpenicillin potassium salt (8). The antibacterial activity of 8 was low, whereas the 6-epimer 9 was inactive. Contary to published information, the 5-phenylpenam derivative 4c could be prepared by the same method.

Synthesis of new antimicrobials. III. Synthesis of chlorine-substituted 4-thiocyanatoaniline and 2-amino-6-chlorobenzothiazole derivatives.

In order to examine their antimicrobial activity, new N-derivatives of chlorine-substituted 4-thiocyanatoanilines (A) and 2-amino-6-chlorobenzothiazole (B) were prepared by the reaction of compound A or B with haloacetyl halides, alkyl chloroformates, phenoxyacetyl chlorides, phenyl isocyanates, or arylaldehydes.

Studies on lactams—XXVII : Synthesis and reactions of 4-carboxy-β-lactam

Reaction of phenoxyacetyl chloride with α-carbomethoxybenzylidine- p-anisidine 1 in presence of triethylamine gave a mixture of E and Z 1-( p-anisyl)-4-carbomethoxy-3-phenoxy-4-phenyl-2-azetidinones 2 which upon hydrolysis with lithium iodide in refluxing pyridine produced the corresponding acids in the ratio of 3:1. A series of substituted β-lactams were prepared by transforming the carboxy group of the E-isomer into the acid chloride, amide, cyano, acid azide, isocyanate, urethane, urea, hydroxymethyl, aldehyde, acetoxy and methoxy groups.