Reactions of 1,2-diaza-1,3-dienes with thiol derivatives: a versatile construction of nitrogen/sulfur containing heterocycles

Cultivating the Passion to Build Heterocycles from 1,2‐Diaza‐1,3‐dienes: the Force of Imagination

“…1,4-Addition/annulation/ring-opening/air-oxidation sequence for the synthesis of 2-iminothiazoline disulfide derivatives 189 starting from DD 1e,f and rhodanine 185. It is noteworthy that the nitrogen atom involved in the formation of the thiazine ring is derived from DD 1, while in our previous communication [59] and many classical syntheses the nitrogen atom is furnished by the aminothiol derivative. [60] The subsequent intramolecular nucleophilic substitution of the hydroxy group by the ureido nitrogen atom produces compounds 200 through a further ring closure (Scheme 39).…”

Synthesis and antimicrobial activity of morpholinyl/piperazinylbenzothiazines

“…1,4-Benzothiazines (III), required for the synthesis of morpholinyl/piperazinylbenzothiazines were synthesized, by the reaction of substituted 2-aminoenzenethiols with b-ketoesters in the presence of dimethyl sulfoxide (DMSO) Attanasi, 2008). The reaction is considered to proceed with the in situ formation of disulphide and subsequent cleavage of S-S bond of morpholinyl/piperazinylbenzothiazines (IV) were synthesized in a single step by the reaction of 4H-1,4-benzothiazines with morpholine/ N-(2-hydroxyethyl)piperazine in aliphatic lower alcohols (Scheme 1).…”

Addition and Cycloaddition Reactions of Phosphinyl- and Phosphonyl-2H-Azirines, Nitrosoalkenes and Azoalkenes

“…Amino- and alkoxy-carbonyl 1,2-diaza-1,3-dienes underwent 1,4-addtion with sulfur nucleophiles such as 1,2-aminothiols [ 47 ] ( Scheme 20 ), thiourea [ 48 ] ( Scheme 21 ) and 3-mercapto-2-ketones [ 49 ] ( Scheme 22 ) producing either functionalized hydrazones or ensuing cyclised heterocycles.…”