Azidotrimethylsilane-mediated Schmidt rearrangement of 2-aryl-1,2,3,4-tetrahydro-1-methylsulfonyl-4-quinolones: non-regioselectivity of carbon migration

Authors
Mphahlele, MJ
Citation
Mj. Mphahlele, Azidotrimethylsilane-mediated Schmidt rearrangement of 2-aryl-1,2,3,4-tetrahydro-1-methylsulfonyl-4-quinolones: non-regioselectivity of carbon migration, J CHEM S P1, (23), 1999, pp. 3477-3482
Citations number
26
Categorie Soggetti
Chemistry & Analysis","Organic Chemistry/Polymer Science
Journal title
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1
ISSN journal
0300922X → ACNP
Issue
23
Year of publication
1999
Pages
3477 - 3482
Database
ISI
SICI code
0300-922X(1999):23<3477:ASRO2>2.0.ZU;2-8
Abstract
Azidotrimethylsilane-mediated Schmidt rearrangement of 2-aryl-1-methylsulfo nyl-1,2,3,4-tetrahydro-4-quinolones in trifluoroacetic acid was investigate d. In contrast to the corresponding 2-aryl-1,2,3,4-tetrahydro-4-quinolone p recursors, the N-methylsulfonyl derivatives displayed non-regioselectivity of carbon migration during nitrogen insertion affording the isomeric ring-e xpanded derivatives via alkyl and aryl migration.