On the mechanism of conversion of 4-carboxy-3,4-dihydro-3-phenyl-1(2H)-isoquinolones to indeno[1,2-c]isoquinolines by thionyl chloride

Xiangshu Xiao, Andrew Morrell, Phillip E. Fanwick, Mark Cushman

Research output: Contribution to journalArticle

13 Scopus citations

Abstract

It has been known for a long time that thionyl chloride can effectively mediate the transformation of 4-carboxy-3,4-dihydro-3-phenyl-1(2H)-isoquinolones to indeno[1,2-c]isoquinolines. The mechanism of this unique transformation, however, remains to be established. Evidence is presented to demonstrate that (1) the two-electron dehydrogenation precedes Friedel-Crafts cyclization and (2) the two-electron dehydrogenation occurs via H-4 deprotonation and subsequent O-sulfinylation of the lactam moiety instead of C-sulfinylation of the carbon α to the carboxyl group.

Original languageEnglish (US)
Pages (from-to)9705-9712
Number of pages8
JournalTetrahedron
Volume62
Issue number41
DOIs
StatePublished - Oct 9 2006

Keywords

  • Indenoisoquinoline
  • Intramolecular Friedel-Crafts reaction
  • Oxidation
  • Thionyl chloride

ASJC Scopus subject areas

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Fingerprint Dive into the research topics of 'On the mechanism of conversion of 4-carboxy-3,4-dihydro-3-phenyl-1(2H)-isoquinolones to indeno[1,2-c]isoquinolines by thionyl chloride'. Together they form a unique fingerprint.

  • Cite this