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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(2H)-imine derivatives

✍ Scribed by María I. García Trimiño; Arturo Macías Hermán Vélez Cabrera Castro; Arístides Rosado Pérez; Dally Moya Argilagos; Anthony Linden; Heinz Heimgartner

Publisher
John Wiley and Sons
Year
1998
Tongue
German
Weight
594 KB
Volume
81
Category
Article
ISSN
0018-019X

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✦ Synopsis

The redction of N,N -dimethyl-2-nitroethene-I,l-diamine (8) with cc,j-unsaturdted dcyl ISOthiOCydndteS 9 dffords 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 Oxiddtive cyclization of 10 with diethyl azodicdrboxylate leads to 4-nitro-1,2-thiazol-5(2H)-lmlne derivatives 12

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