Chimie des radioprotecteurs: synthèse d'alkylamino-2 éthanethiols encombrés sur l'atome d'azote

Abstract

Synthesis of 2-alkylaminoethanethiols with a tertiary group fixed to the nitrogen atom has been achieved. A very convenient method of access to such 2-alkylaminoethanethiols with one, two, and three allyl substituents is the reaction between allylic organomagnesium compounds and thiazolidines, 2-alkylthiazolines, and 2-methylthiothiazolines respectively.

Overview of the Chemistry of 2-Thiazolines

“…66 Thiazoline-thiazolidine transformation and subsequent cleavage with HgCl 2 were extended to the preparation of R,R-disubstituted β-ethylenic ketones. 67 The β-ethylenic thiazolidine precursors 144 were obtained by addition of allylic Grignard reagent 143 to 2-alkyl-2-thiazolines 142. Conventional mercuric chloride cleavage afforded the expected ketones 145 (Scheme 50).…”

Recent advances in the synthesis and utility of thiazoline and its derivatives

“…Thiazolines exhibit reactivity due to the presence of two nucleophilic centres localized on the nitrogen and sulfur atoms, along with an electrophilic centre on the carbon atom of the CN bond. This versatility makes thiazolines as valuable reagents in the synthesis of diverse compounds, including carbonyls, 47,48 β-amino thiols, 49,50 thiazoles, 51,52 and thiazolinium salts 53 (Fig. 5).…”

2-Methyl-2-thiazoline

“…12 1,2-Addition of allylic Grignard reagents to the imine double bond of 2-methyl-2-thiazoline (and derivatives) occurs with transposition of the allylic double bond in good yields (eq 11). 4 Thiazoline hydrolysis affords the two-carbon extended α,α-disubstituted β-ethylenic methyl ketones. In addition to the title reagent, similar two-carbon extension synthons, such as 2-Methylbenzothiazole (1) 13 and 4,5-dihydroimidazoles (e.g.…”