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Updated: Aug 6, 2026

Facile Preparation of 4-Substituted Quinazoline Derivatives
Published on: February 15, 2016
Preparation of 1,4-Naphthoquinones and 9,10-Anthraquinones through Brønsted Acid-Catalyzed [4+2] Cycloaddition
Kai Feuer1, Peter R Schreiner1
1Institute of Organic Chemistry, Justus Liebig University, 35392Giessen, Germany.
Abstract:
We report the synthesis of substituted 1,4-naphthoquinones (1,4-NQs) and 9,10-anthraquinones (9,10-AQs) via Brønsted acid-catalyzed [4+2] cycloaddition of simple butadienes and p-benzoquinones to give 5,8-dihydro-1,4-NQs under ambient conditions in up to 90% yield. Subsequent dehydrogenation gives the corresponding 1,4-NQs (62-98%), while a second Brønsted acid-catalyzed [4+2] cycloaddition (that can be performed in one pot) generates 1,4,5,8-tetrahydro-9,10-AQs (71-88%). This enables the synthesis of a variety of highly substituted quinones and acenes.
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