Synthesis and Characterization of .ALPHA.-Bromo 5-Methyl Tetrazoles from Long Chain Fatty Alkenoates

Abstract

In view of synthetic utility and biological importance of tetrazole derivatives, 1-phenylethyl undec-10-enoate, 1-phenylethyl (Z)-octadec-9-enoate and 1-phenylethyl (Z)-12hydroxyoctadec-9-enoate have been converted into their a-bromo 5-methyl tetrazole derivatives, using bromine, acetonitrile and sodium azide as reagents. The structure elucidation of the prepared compounds is based on elemental analysis and spectral data.

Acetonitrile as a Building Block and Reactant

“…213 Other alkenes have been reacted this way using AlCl 3 /Br 2 . 214,215 Scheme 41 Multicomponent reaction of acetonitrile/azide/alkene to give 5-methyl-1H-tetrazoles Ketones (acetone and acetophenone) and acetonitrile react in the presence of Fe(NO 3 ) 3 or cerium ammonium nitrate to give 1,2,4-oxadiazoles (Scheme 42). 216 The reaction proceeds by nitration to form an α-nitro ketone, and this is then postulated to decompose by elimination of water to yield a nitrile oxide which undergoes 1,3-dipolar addition with acetonitrile.…”

Synthesis, Antibacterial and Antifungal Activity of Some Novel 3,5‐Disubstituted‐1H‐1,2,4‐triazoles

“…The present work is in continuation of our study on the synthesis of heterocycles from such acids. Tetrazoles, [27,28] pyrazolines [29], tetrazines [30,31], spiro [oxathiolane-2,29-dihydrotetrazoles] [32], aziridines [33], and triazines [34] have been previously prepared in our lab. Cyanoethoxy and morpholine derivatives of hydroxy long-chain acids [35] and fatty esters [36] showed significant antifungal and antibacterial activity.…”

Facile One-Pot Synthesis of N-acyl-1H-1,2,3-benzotriazoles from Internal and Terminal Olefinic Fatty Acids and Their Antimicrobial Screening

“…To the best of our knowledge no work seems to have been done on olefinic fatty N-acyl-1H-1,2,3-benzotriazoles, the present work is in continuation of our study on the derivatization of olefinic fatty acids. Tetrazoles 7,8) , pyrazolines 9) , tetrazine 10,11) and spiro [oxathiolane-2,2 -dihydrotetrazoles] 12) and aziridines 13) have been previously prepared in our lab. Cyanoethoxy and morphline derivatives of hydroxy fatty acids 14) and fatty esters 15) showed significant antifungal and antibacterial activity respectively.…”