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

Yasuyuki KITA; Masahiro EGI; Makoto OHTSUBO; Toyokazu SAIKI; Akiko OKAJIMA; Takeshi TAKADA; Hirofumi TOHMA

doi:10.1248/cpb.47.241

Yasuyuki KITA, Masahiro EGI, Makoto OHTSUBO, Toyokazu SAIKI, Akiko OKAJIMA, Takeshi TAKADA, Hirofumi TOHMA

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Keywords: quinone imine ketal, quinone imine, hypervalent iodine(III) reagent, phenyliodine(III) bis (trifluoroacetate)

JOURNAL FREE ACCESS

1999 Volume 47 Issue 2 Pages 241-245

DOI https://doi.org/10.1248/cpb.47.241

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Abstract

Novel and efficient syntheses of quinone imine ketals (2a-j) and quinone imines (4a-h) from substituted phenol ethers (1a-k) bearing an alkyl azido side-chain using the combination of hypervalent iodine(III) reagent, phenyliodine(III) bis(trifluoroacetate) (PIFA) and trimethylsilyl trifuoromethanesulfonate (TMSOTf), have been developed.

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