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Updated: Jul 20, 2026

Facile Preparation of 4-Substituted Quinazoline Derivatives
Published on: February 15, 2016
Intermolecular [4 + 2] cycloaddition of o-quinodimethanes derived from ene-bis(sulfinylallenes)
Shinji Kitagaki1, Kumiko Katoh, Kazuhiro Ohdachi
1Division of Pharmaceutical Sciences, Graduate School of Natural Science and Technology, Kanazawa University, Kakuma-machi, Kanazawa 920-1192, Japan. kitagaki@p.kanazawa-u.ac.jp
Abstract:
Intermolecular [4 + 2] cycloaddition of o-quinodimethanes, prepared in situ from ene-bis(propargyl alcohols) and benzenesulfenyl chloride via ene-bis(sulfinylallene) formation, was investigated. Benzene-bridged bis(propargyl alcohols) reacted with both electron-deficient and electron-rich olefins to give the corresponding [4 + 2] cycloadducts. Ethylene-bridged bis(propargyl alcohols) underwent similar cycloaddition with electron-deficient olefins. Construction of some heterocycles based on the newly developed sequential reaction is also described.
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