Download PDF
Synthesis 2004(5): 775-778  
DOI: 10.1055/s-2004-815995
SPECIALTOPIC
© Georg Thieme Verlag Stuttgart · New York

Regio- and π-Facial Selective Cycloadditions Involving 2-Phenyl-4-dimethylamino-1-thia-3-azabuta-1,3-diene and Allenic Esters: An Efficient Route to Novel 6-Alkylidene-6H-2-phenyl-5-ethoxycarbonyl-1,3-thiazines

M. P. S. Ishar*, Ashish Kapur, Tilak Raj, Navdeep K. Girdhar, Amritpal Kaur
Department of Pharmaceutical Sciences, Guru Nanak Dev University, Amritsar - 143005, Punjab, India
Fax: +91(183)2258820; e-Mail: mpsishar@angelfire.com;
Further Information

Publication History

Received 6 February 2004
Publication Date:
03 March 2004 (online)

   Buy Article Permissions and Reprints All articles of this category
Zoom Image

Abstract

2-Phenyl-4-dimethylamino-1-thia-3-azabuta-1,3-diene (4) undergoes regio- and stereoselective [4+2] cycloadditions with allenic esters on refluxing in CH2Cl2-benzene and the initially formed cycloadducts 6 furnish, after elimination of dimethylamine, novel (E/Z)-6-alkylidene-6H-2-phenyl-5-ethoxycarbonyl-1,3-thiazines 7 and 8 in high yields. In the case of reaction with ethyl 2-methylbuta-2,3-dienoate, the adduct 6e has been isolated in very high yields.

Key words

1-thia-3-azabuta-1,3-diene - allenic esters - cycloadditions - 1,3-thiazines - hetero Diels-Alder reaction