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Platinum‐Catalyzed Formation of Cyclic‐Ketone‐Fused Indoles from N ‐(2‐Alkynylphenyl)lactams
Author(s) -
Li Guotao,
Huang Xiaogen,
Zhang Liming
Publication year - 2007
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200702931
Subject(s) - alkyne , cycloisomerization , substituent , amide , intramolecular force , chemistry , alkyl , ring (chemistry) , catalysis , medicinal chemistry , aryl , ketone , stereochemistry , organic chemistry
An oxygen atmosphere aids the efficient formation of highly substituted ring‐fused indoles by the versatile title reaction through an initial cyclization followed by the sequential migration of two groups. The cycloisomerization can be viewed as a net intramolecular insertion of one end of the alkyne into the lactam amide bond with concurrent migration of the substituent at the alkyne terminus (see scheme; n =0–2; R=alkyl, alkenyl, aryl, H; R′=OMe, Br, CO 2 Et).