A [4+2] cycloaddition of push-pull styrenes to 1,2-naphthoquinone 1-methides: a synthesis of 2-aryl-2,3-dihydro-1H-benzo[f]chromenes

IF 1.4 4区化学 Q3 CHEMISTRY, ORGANIC

Chemistry of Heterocyclic Compounds Pub Date : 2024-01-10 DOI:10.1007/s10593-024-03267-6

Kirill S. Korzhenko, Anastasiya S. Yushkova, Darya A. Rashchepkina, Oleg P. Demidov, Dmitry V. Osipov, Vitaly A. Osyanin

引用次数: 0

Abstract

A regioselective and trans-diastereoselective method for the preparation of 2-aryl-2,3-dihydro-1H-benzo[f]chromenes based on 2-naphthol Mannich bases as precursors of 1,2-naphthoquinone 1-methides and highly polarized β-(N,N-dimethylamino)styrene was developed. The resulting cycloadducts were transformed into cyclic acetals and hemiacetals as well as introduced into the Cope reaction leading to 2-aryl-1H-benzo[f]chromenes.

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推挽式苯乙烯与 1,2-萘醌 1-甲酯的[4+2]环加成反应：2-芳基-2,3-二氢-1H-苯并[f]色烯的合成

以 2-萘酚曼尼希碱为前体，以 1,2-萘醌 1-甲酯和高度极化的 β-(N,N-二甲基氨基)苯乙烯为基础，开发了一种具有区域选择性和反式非对映选择性的制备 2-芳基-2,3-二氢-1H-苯并[f]色烯的方法。由此产生的环加载产物被转化为环乙醛和半乙醛，并被引入科普反应，生成 2-芳基-1H-苯并[f]色烯。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

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来源期刊

Chemistry of Heterocyclic Compounds 化学-有机化学

CiteScore

2.90

自引率

13.30%

发文量

审稿时长

1 months

期刊介绍： The international journal Chemistry of Heterocyclic Compounds publishes original papers, short communications, reviews, and mini-reviews dealing with problems in the field of heterocyclic chemistry in Russian and English. The Journal also publishes reviews and annotations on new books and brief reports on conferences in the field of heterocyclic chemistry, as well as commemoratives dedicated to prominent heterocyclic chemists.