IMINIUM CARBONIC-ACID DERIVATIVE SALTS .11. SYNTHESIS OF N,S-CONTAINING HETEROBICYCLES FROM N-PROTECTED 2-METHYLTHIO-1,3-THIAZINIUM AND 2-METHYLTHIOTHIAZOLIUM SALTS .3. REACTION OF N-PROTECTED 2-METHYLTHIO-1,3-THIAZINIUM AND 2-METHYLTHIOTHIAZOLIUM SALTS WITH 3-AMINO-2-CYANO-3-ARYLACRYLONITRILES

Citation
W. Hanefeld et al., IMINIUM CARBONIC-ACID DERIVATIVE SALTS .11. SYNTHESIS OF N,S-CONTAINING HETEROBICYCLES FROM N-PROTECTED 2-METHYLTHIO-1,3-THIAZINIUM AND 2-METHYLTHIOTHIAZOLIUM SALTS .3. REACTION OF N-PROTECTED 2-METHYLTHIO-1,3-THIAZINIUM AND 2-METHYLTHIOTHIAZOLIUM SALTS WITH 3-AMINO-2-CYANO-3-ARYLACRYLONITRILES, Journal of heterocyclic chemistry, 33(6), 1996, pp. 1903-1907
Citations number
3
Categorie Soggetti
Chemistry Inorganic & Nuclear
ISSN journal
0022152X
Volume
33
Issue
6
Year of publication
1996
Pages
1903 - 1907
Database
ISI
SICI code
0022-152X(1996)33:6<1903:ICDS.S>2.0.ZU;2-L
Abstract
N-Boc-protected 2-methylthio-1,3-thiazinium 1 and 2-methylthiothiazoli um iodides 2, 3 obtained from the corresponding 3,4,5,6-tetrahydro-2H- 1,3-thiazine-2-thiones and thiazolidine-2-thiones by the action of met hyl iodide were reacted with 3-amino-2-cyano-3-arylacrylonitriles form ing the cyclic isothioureas 5-7. The protection group was removed with trifluoroacetic acid whereupon the desired cyclisation to 3,4-dihydro -2H,6H-pyrimido[2,1-b][1,3]thiazines 8a-c, 8a'-c' and thiazolo[3,2-b]p yrimidines 9a,b, 9a',b', 10a,b took place.