Chemistry of 1,3-thiazin-4-ones and their derivatives, 1995 - mid-2018

Abstract

This review updates an earlier review published in 1996 by Ryabukhin, Korzhavina, and Suzdalev, which covered the literature through 1994. It deals with the synthesis and reactivity of 1,3-thiazin-4-ones and their derivatives. These include reduced compounds, 2-imino or 2-amino compounds, compounds with fused arenes or heterocycles, bridged compounds, and compounds combining various of these attributes.

Crystal structures of rac-2,3-diphenyl-2,3,5,6-tetrahydro-4H-1,3-thiazine-1,1,4-trione and N-[(2S,5R)-1,1,4-trioxo-2,3-diphenyl-1,3-thiazinan-5-yl]acetamide

“…The 2,3-dihydro-4H-1,3-thiazin-4-ones are a group of sixmembered heterocycles with a wide range of biological activity (Ryabukhin et al, 1996;Silverberg & Moyer, 2019). Surrey's research (Surrey et al, 1958;Surrey, 1963a,b) resulted in the discovery of two drugs, the antianxiety and muscle relaxant chlormezanone, C 11 H 12 ClNO 3 S, [2-(4-chlorophenyl)-3-methyl-2,3,5,6-tetrahydro-4H-1,3-thiazin-4-one 1,1-dioxide] (O 'Neil, 2006;Tanaka & Horayama, 2005) and the muscle relaxant dichlormezanone, C 11 H 11 Cl 2 NO 3 S, [2-(3,4-dichlorophenyl)-3-methyl-2,3,5,6-tetrahydro-4H-1,3-thiazin-4-one 1,1dioxide] (Elks & Ganellin, 1990).…”

Crystal structures of the sulfones of 2,3-diphenyl-2,3-dihydro-4H-1,3-benzothiazin-4-one and 2,3-diphenyl-2,3-dihydro-4H-pyrido[3,2-e][1,3]thiazin-4-one

“…The 2,3-dihydro-4H-1,3-thiazin-4-ones are a group of sixmembered heterocycles with a wide range of biological activity (Ryabukhin et al, 1996;Silverberg & Moyer, 2019). Surrey's research (Surrey et al, 1958, Surrey, 1963a resulted in the discovery of two drugs, the antianxiety and muscle relaxant chlormezanone, 2-(4-chlorophenyl)-3-methyl-2,3,5,6tetrahydro-4H-1,3-thiazin-4-one 1,1-dioxide (O'Neil, 2006;Tanaka & Hirayama, 2005) and the muscle relaxant dichlormezanone, 2-(3,4-dichlorophenyl)-3-methyl-2,3,5,6-tetrahydro-4H-1,3-thiazin-4-one 1,1-dioxide (Elks & Ganellin, 1990).…”

T3P-Promoted Synthesis of a Series of 2-Aryl-3-phenyl-2,3-dihydro-4H-pyrido[3,2-e][1,3]thiazin-4-ones and Their Activity against the Kinetoplastid Parasite Trypanosoma brucei

“…There are only a modest number of 2,3-dihydro-4H-pyrido[3,2-e][1,3]thiazin-4-ones reported in the literature, and the number grows quite small when there is an aryl group on the nitrogen of the 1,3-thiazin-4-one ring [1,2,[8][9][10]. A common method used for preparation of a variety of 2,3-dihydro-4H-1,3-thiazin-4-ones is the cyclization of an imine with a 3-thiocarboxylic acid [11]. However, it is known that N-aryl imines are less reactive in the preparation of similar 2,3-dihydro-4H-1,3-thiazin-4-ones than N-alkyl imines [12][13][14].…”