An Efficient Synthesis of peri-Hydroxy Aromatic Compounds: A Strong Base-Induced [4 + 2]Cycloaddition of 4-Phenylthio-Substituted Homophthalic Anhydrides with Various Sulfinyl-Substituted Dienophiles

Yasuyuki Kita; Kiyosei Iio; Akiko Okajima; Yoshifumi Takeda; Ken-ichi Kawaguchi; Brendan A. Whelan; Shuji Akai

doi:10.1055/s-1998-1642

Synlett 1998; 1998(3): 292-294
DOI: 10.1055/s-1998-1642

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An Efficient Synthesis of peri-Hydroxy Aromatic Compounds: A Strong Base-Induced [4 + 2]Cycloaddition of 4-Phenylthio-Substituted Homophthalic Anhydrides with Various Sulfinyl-Substituted Dienophiles

Yasuyuki Kita^* , Kiyosei Iio, Akiko Okajima, Yoshifumi Takeda, Ken-ichi Kawaguchi, Brendan A. Whelan, Shuji Akai

^*Faculty of Pharmaceutical Sciences, Osaka University, 1-6, Yamada-oka, Suita, Osaka 565, Japan; Fax +81 6-8 79-82 29; E-mail: kita@phs.osaka-u.ac.jp

Abstract

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As an extension of the strong base-induced [4 + 2]cycloaddition of homophthalic anhydrides studied previously, we found a general and versatile synthesis of p-phenylthio substituted phenols by the reaction of 4-phenylthio-substituted homophthalic anhydrides and various dienophiles. The use of the sulfinyl-substituted dienophile is essential to produce the desired reaction under mild conditions in good yield.

strong base-induced [4 + 2]cycloaddition - 4-phenylthio-substituted homophthalic anhydride - peri-hydroxy aromatic compound - aromatic Pummerer-type reaction

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