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

✍ Scribed by Nobin Terang; Barun K Mehta; H Ila; H Junjappa

• Publisher: Elsevier Science
• Year: 1998
• Tongue: French
• Weight: 754 KB
• Volume: 54
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(98)00790-x

✦ Synopsis

An efficient method for the synthesis of novel 2-methylthio-2-alkyl/aryl-l-nitrocthylenes 2 has been developed via conjugate addition-elimination of organocopper reagents to nitroketene dithioacetal 1 in the presence of TMSCI. The product introethylenes 2 have been further utilized for the synthesis of substituted 3-nitro-2-alkyl/arylpyrroles 5 by their reaction with aminoacetaldehyde dimethylacetal followed by acid catalyzed cyclization in ethereal HCI. The reaction of 2 with propargyl alcohol has also been investigated.