REACTION OF N,N'-DIMETHYL-2-NITROETHENE-1,1-DIAMINE WITH ALPHA,BETA-UNSATURATED ACYL ISOTHIOCYANATES - PREPARATION OF 1,3-THIAZIN-4-ONE AND4-NITRO-1,2-THIAZOL-5(2H)-IMINE DERIVATIVES

Authors
TRIMINO MIG CABRERA AM CASTRO HV PEREZ AR ARGILAGOS DM LINDEN A HEIMGARTNER H
Citation
Mig. Trimino et al., REACTION OF N,N'-DIMETHYL-2-NITROETHENE-1,1-DIAMINE WITH ALPHA,BETA-UNSATURATED ACYL ISOTHIOCYANATES - PREPARATION OF 1,3-THIAZIN-4-ONE AND4-NITRO-1,2-THIAZOL-5(2H)-IMINE DERIVATIVES, Helvetica Chimica Acta, 81(4), 1998, pp. 718-728
Citations number
38
Categorie Soggetti
Chemistry
Journal title
Helvetica Chimica Acta → ACNP
ISSN journal
0018019X
Volume
81
Issue
4
Year of publication
1998
Pages
718 - 728
Database
ISI
SICI code
0018-019X(1998)81:4<718:RONWA>2.0.ZU;2-V
Abstract
The reaction of N,N'-dimethyl-7-nitroethene-1,1-diamine (8) with alpha ,beta-unsaturated acyl isothiocyanates 9 affords 3,3-diamino-2-nitroac rylthioamides 10 (Scheme 2) in moderate-to-good yields. Cyclization of 10 under acidic conditions gives 1,3-thiazin-4-one derivatives of typ e 11. Oxidative cyclization of 10 with diethyl azodicarboxylate leads to 4-nitro-1,2-thiazol-5(2H)-imine derivatives 12.