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4-二甲氨基吡啶催化的亚烷基吡唑啉酮与硝基烯烃之间的多米诺劳乌特-库里尔环化反应:通向四氢吡喃并[2,3-]吡唑类化合物的途径

DMAP Catalyzed Domino Rauhut-Currier Cyclization Reaction between Alkylidene Pyrazolones and Nitro-olefins: Access to Tetrahydropyrano[2,3-]pyrazoles.

作者信息

Bania Nimisha, Mondal Buddhadeb, Ghosh Sounak, Pan Subhas Chandra

机构信息

Department of Chemistry, Indian Institute of Technology Guwahati, Guwahati 781039, India.

出版信息

J Org Chem. 2021 Mar 5;86(5):4304-4312. doi: 10.1021/acs.joc.0c02871. Epub 2021 Feb 17.

DOI:10.1021/acs.joc.0c02871
PMID:33593067
Abstract

Herein, we employ unsaturated pyrazolones in the Rauhut-Currier reaction for the first time. A domino Rauhut-Currier cyclization reaction has been developed between unsaturated pyrazolones and nitro-olefins. The trisubstituted tetrahydropyrano[2,3-]pyrazoles were obtained in moderate to high yields with excellent diastereoselectivities. A few applications including a synthesis of disubstituted tetrahydropyrano[2,3-]pyrazole have been demonstrated. A preliminary catalytic asymmetric version of this process was also studied with chiral DMAP catalysts.

摘要

在此,我们首次将不饱和吡唑啉酮用于劳乌特-库里尔反应。已开发出一种不饱和吡唑啉酮与硝基烯烃之间的多米诺劳乌特-库里尔环化反应。以中等至高产率获得了具有优异非对映选择性的三取代四氢吡喃并[2,3 - ]吡唑。已展示了一些应用,包括二取代四氢吡喃并[2,3 - ]吡唑的合成。还使用手性DMAP催化剂对该过程的初步催化不对称版本进行了研究。

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