DBU 催化β′和δ-乙酰氧基异烯酸酯与苯并氧硫辛-二氧化物和苯基噻唑酮的(3 + 3)环化反应：吡喃氧硫杂环丁烷和吡喃噻唑的合成

IF 1.7 4区化学 Q3 CHEMISTRY, MULTIDISCIPLINARY Journal of Chemical Sciences Pub Date : 2024-10-04 DOI:10.1007/s12039-024-02302-5

Asif Ali Qureshi, Sachin Chauhan, K C Kumara Swamy

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引用次数: 0

摘要

本文介绍了在 DBU（DBU = 1,8-二氮杂双环[5.4.0]十一-7-烯）催化下，乙酰氧基异烯酸酯与可烯化的羰基底物发生的环化反应。在 DBU 催化下，乙酰氧基异戊酸酯与双功能亲核物苯并氧硫辛-二氧化物和苯并噻唑酮发生（3 + 3）环化反应，生成融合的 4H-pyrans 。在 DBU 催化下，乙酰氧基异烯酸酯与（3 + 3）苯并氧硫烷-二氧化物和苯并噻唑酮发生环化反应，生成吡喃氧硫烷和吡喃噻唑。

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DBU catalyzed (3 + 3) annulation of β′ and δ-acetoxy allenoates with benzo-oxathiin-dioxide and phenylthiazolone: Synthesis of pyrano-oxathiines and pyrano-thiazoles

Annulation reactions involving acetoxy allenoates and enolizable carbonyl substrates under DBU (DBU = 1,8-diazabicyclo[5.4.0]undec-7-ene) catalysis is described in this paper. Thus DBU catalyzed (3 + 3) annulation reactions of acetoxy allenoates with the bifunctional nucleophiles benzo-oxathiin-dioxide and phenylthiazolone afford fused 4H-pyrans. Both β′-acetoxy allenoates and δ-acetoxy allenoates undergo this annulation to give pyrano-oxathiines or pyrano-thiazoles.

Graphical abstract

Acetoxy allenoates undergo facile (3 + 3) annulation with benzo-oxathiin-dioxide and phenylthiazolone under DBU catalysis to afford pyrano-oxathiines and pyrano-thiazoles.

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来源期刊

Journal of Chemical Sciences CHEMISTRY, MULTIDISCIPLINARY-

CiteScore

3.10

自引率

5.90%

发文量

107

审稿时长

1 months

期刊介绍： Journal of Chemical Sciences is a monthly journal published by the Indian Academy of Sciences. It formed part of the original Proceedings of the Indian Academy of Sciences – Part A, started by the Nobel Laureate Prof C V Raman in 1934, that was split in 1978 into three separate journals. It was renamed as Journal of Chemical Sciences in 2004. The journal publishes original research articles and rapid communications, covering all areas of chemical sciences. A significant feature of the journal is its special issues, brought out from time to time, devoted to conference symposia/proceedings in frontier areas of the subject, held not only in India but also in other countries.