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 language | English (US) |
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Pages (from-to) | 9705-9712 |
Number of pages | 8 |
Journal | Tetrahedron |
Volume | 62 |
Issue number | 41 |
DOIs | |
State | Published - Oct 9 2006 |
Externally published | Yes |
Keywords
- Indenoisoquinoline
- Intramolecular Friedel-Crafts reaction
- Oxidation
- Thionyl chloride
ASJC Scopus subject areas
- Biochemistry
- Drug Discovery
- Organic Chemistry