Syntheses of 4 and 5‐alkylsulfonylimidazoles

Abstract

A series of isomeric 4 and 5‐alkylsulfonyl, alkylsulfinylimidazoles 9,10 were prepared by two general methods. Chlorosulfonation of imidazole afforded 4(5)‐chlorosulfonylimidazoles 2, 4, 5. The chlorosulfonyl derivatives were reduced, alkylated and oxidized to give 9 and 10. In the second method 2, 4, 5 were converted to sodium sulfinate 8 and reacted with alkyl halides to afford the title compound 9.

Syntheses of substituted pyrrolo[2,3‐d]imidazole‐5‐carboxylates and substitued pyrrolo[3,2‐d]imidazole‐5‐carboxylates

“…The N-CH 2 resonance of 10 (5.6 ppm) is more deshielded than that of 11 (5.15 ppm). In addition, 1 H-nmr spectral data of 10 were similar to previously reported data [8].…”

“…The starting 5-hydroxymethyl-2-mercapto-1-substituted-benzylimidazoles (1) could be obtained from benzylation of 2-mercapto-5-formylimidazole according to the procedure reported previously [8]; however, this reaction would give a mixture of two compounds. Therefore, we have decided to use a direct method for the preparation of 1.…”

Synthesis and analgesic activity of new 1,3,4-oxadiazoles and 1,2,4-triazoles

“…Compounds 4 and 5 were prepared by oxidation of ester 3a with hydrogen peroxide (Shafiee et al, 1998;Brannigan et al, 1976 respectively. 5-Aryl-1,3,4-oxadiazole-2(3H)-thiones 7a-7d were prepared by reaction of hydrazides 6a-6d with KOH and CS 2 .…”

Synthesis of novel 2‐(2‐methylsulfonyl‐1‐methyl‐1H‐imidazol‐5‐yl)‐5‐(alkylsulfonyl)‐1,3,4‐thiadiazoles

“…Reaction of 5-hydroxymethyl-2-mercapto-1-methylimidazole (1) with methyl iodide afforded 5-hydroxymethyl-2-methylthio-1-methylimidazole (2) [14]. Oxidation of alkylthio group with m-chloroperbenzoic acid gave compound 3 [15]. Oxidation of hydroxyl group at 5 position of compound 3 with activated manganese (IV) oxide yielded the desired aldehyde 4 [16].…”