Hypervalent iodine(III)-induced intramolecular cyclization reaction of substituted phenol ethers with an alkyl azido side-chain: A novel and efficient synthesis of quinone imine derivatives

Authors
Kita, Y Egi, M Ohtsubo, M Saiki, T Okajima, A Takada, T Tohma, H
Citation
Y. Kita et al., Hypervalent iodine(III)-induced intramolecular cyclization reaction of substituted phenol ethers with an alkyl azido side-chain: A novel and efficient synthesis of quinone imine derivatives, CHEM PHARM, 47(2), 1999, pp. 241-245
Citations number
33
Categorie Soggetti
Chemistry & Analysis
Journal title
CHEMICAL & PHARMACEUTICAL BULLETIN
ISSN journal
00092363 → ACNP
Volume
47
Issue
2
Year of publication
1999
Pages
241 - 245
Database
ISI
SICI code
0009-2363(199902)47:2<241:HIICRO>2.0.ZU;2-B
Abstract
Novel and efficient syntheses of quinone imine ketals (2a-j) and quinone im ines (4a-h) from substituted phenol ethers (1a-k) bearing an alkyl azido si de-chain using the combination of hypervalent iodine(III) reagent, phenylio dine(III) bis(trifluoroacetate) (PIFA) and trimethylsilyl trifluoromethanes ulfonate (TMSOTf), have been developed.