An efficient synthesis of spiro- β-lactams having sulfenyl, sulfinyl and sulfonyl moiety

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• 作者：RESHMA ; RENU ARORA ; GEETA HUNDAL ; AMAN BHALLA ; S S BARI
• 关键词：β ; lactams ; intrasulfenyl cyclization ; dehalogenation ; sulfoxide ; sulfone
• 刊名：Journal of Chemical Sciences
• 出版年：2015
• 出版时间：November 2015
• 年：2015
• 卷：127
• 期：11
• 页码：1957-1966
• 全文大小：799 KB
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• 作者单位：RESHMA (1)
  RENU ARORA (2)
  GEETA HUNDAL (3)
  AMAN BHALLA (4)
  S S BARI (4)
  
  1. D. A. V. College, Sector 10, Chandigarh, India
  2. University Institute of Engineering and Technology, Panjab University, Chandigarh, India
  3. Department of Chemistry, Guru Nanak Dev University, Amritsar, India
  4. Department of Chemistry and Centre of Advanced studies in Chemistry, Panjab University, Chandigarh, 160014, India
  
• 刊物类别：Chemistry and Materials Science
• 刊物主题：Chemistry
  Chemistry
  
• 出版者：Springer India
• ISSN：0973-7103

文摘

An efficient and a facile route to spiro- β-lactams is described. 3-allyl-3-methylthio- β-lactams, which are synthesized through a Lewis acid mediated C-3 alkylation of the trans-3-chloro-3-methylthio- β-lactams, undergo a facile intrasulfenyl cyclization reaction in the presence of halogens like bromine and iodine to give spiro β-lactams in good yield. These halospiro- β-lactams are then subjected to dehalogenation reaction using Raney-nickel. The resulting spiro- β-lactams are further transformed into their sulfinyl and sulfonyl derivatives by using m-chloroperbenzoic acid as an oxidant.