TRIMETHYLSILYL CHLORIDE ASSISTED CONJUGATE ADDITION-ELIMINATION OF ORGANOCOPPER REAGENTS TO 2-BIS(METHYLTHIO) NITROETHYLENE - AN EFFICIENT AND HIGHLY STEREOSELECTIVE SYNTHESIS OF 2-METHYLTHIO-2-ALKYL ARYL-1-NITROETHYLENES AND THEIR APPLICATION FOR SYNTHESIS OF NITROHETEROCYCLES/

Authors
TERANG N MEHTA BK ILA H JUNJAPPA H
Citation
N. Terang et al., TRIMETHYLSILYL CHLORIDE ASSISTED CONJUGATE ADDITION-ELIMINATION OF ORGANOCOPPER REAGENTS TO 2-BIS(METHYLTHIO) NITROETHYLENE - AN EFFICIENT AND HIGHLY STEREOSELECTIVE SYNTHESIS OF 2-METHYLTHIO-2-ALKYL ARYL-1-NITROETHYLENES AND THEIR APPLICATION FOR SYNTHESIS OF NITROHETEROCYCLES/, Tetrahedron, 54(42), 1998, pp. 12973-12984
Citations number
34
Categorie Soggetti
Chemistry Inorganic & Nuclear
Journal title
Tetrahedron → ACNP
ISSN journal
00404020
Volume
54
Issue
42
Year of publication
1998
Pages
12973 - 12984
Database
ISI
SICI code
0040-4020(1998)54:42<12973:TCACAO>2.0.ZU;2-W
Abstract
An efficient method for the synthesis of novel 2-methylthio-2-alkyl/ar yl-1-nitroethylenes 2 has been developed via conjugate addition-elimin ation of organocopper reagents to nitroketene dithioacetal 1 in the pr esence of TMSCl. The product nitroethylenes 2 have been further utiliz ed for the synthesis of substituted 3-nitro-2-alkyl/arylpyrroles 5 by their reaction with aminoacetaldehyde dimethylacetal followed by acid catalyzed cyclization in ethereal HCl. The reaction of 2 with propargy l alcohol has also been investigated (C) 1998 Elsevier Science Ltd. Al l rights reserved.