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Reaction of N,N '‐dimethyl‐2‐nitroethene‐1, 1‐diamine with α,ß‐unsaturated acyl isothiocyanates: Preparation of 1,3‐thiazin‐4‐one and 4‐nitro‐1,2‐thiazol‐5(2 H )‐imine derivatives
Author(s) -
Trimiño María I. García,
Cabrera Castro Arturo Macías Hermán Vélez,
Rosado Pérez Arístides,
Argilagos Dally Moya,
Linden Anthony,
Heimgartner Heinz
Publication year - 1998
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19980810321
Subject(s) - chemistry , diamine , medicinal chemistry , imine , nitro , organic chemistry , catalysis , alkyl
The reaction of N,N '‐dimethyl‐2‐nitroethene‐1,1‐diamine (8) with α,ß‐unsaturated acyl isothiocyanates 9 affords 3,3‐diamino‐2‐nitroacrylthioamides 10 ( Scheme 2 ) in moderate‐to‐good yields. Cyclization of 10 under acidic conditions gives 1,3‐thiazin‐4‐one derivatives of type 11 . Oxidative cyclization of 10 with diethyl azodicaboxylate leads to 4‐nitro‐1,2‐thiazol‐5(2 H )‐imine derivatives 12 .