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通过碱介导的邻羟基查耳酮与2-溴烯丙基砜的环化反应简便合成4H-色烯衍生物。

Facile synthesis of 4H-chromene derivatives via base-mediated annulation of ortho-hydroxychalcones and 2-bromoallyl sulfones.

作者信息

Thadkapally Srinivas, Kunjachan Athira C, Menon Rajeev S

机构信息

Medicinal Chemistry and Pharmacology Division, CSIR-Indian Institute of Chemical Technology, Hyderabad 500 007, India.

出版信息

Beilstein J Org Chem. 2016 Jan 6;12:16-21. doi: 10.3762/bjoc.12.3. eCollection 2016.

DOI:10.3762/bjoc.12.3
PMID:26877804
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC4734429/
Abstract

The cesium carbonate-mediated reaction of 2-bromoallyl sulfones and ortho-hydroxychalcones furnished 3-arylsulfonyl-4H-chromene derivatives in 58-67% yield (18 examples). 2-Bromoallyl sulfones functioned as synthetic surrogates for allenyl sulfones in the reaction.

摘要

碳酸铯介导的2-溴烯丙基砜与邻羟基查耳酮的反应以58 - 67%的产率得到了3-芳基磺酰基-4H-色烯衍生物(18个实例)。在该反应中,2-溴烯丙基砜作为联烯基砜的合成替代物。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/87d8/4734429/9b1406f9c7c2/Beilstein_J_Org_Chem-12-16-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/87d8/4734429/d9997146e349/Beilstein_J_Org_Chem-12-16-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/87d8/4734429/b4f7ba64121f/Beilstein_J_Org_Chem-12-16-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/87d8/4734429/ded549ab9f9c/Beilstein_J_Org_Chem-12-16-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/87d8/4734429/ed5319ad5b1d/Beilstein_J_Org_Chem-12-16-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/87d8/4734429/e22433a07ac4/Beilstein_J_Org_Chem-12-16-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/87d8/4734429/9b1406f9c7c2/Beilstein_J_Org_Chem-12-16-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/87d8/4734429/d9997146e349/Beilstein_J_Org_Chem-12-16-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/87d8/4734429/b4f7ba64121f/Beilstein_J_Org_Chem-12-16-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/87d8/4734429/ded549ab9f9c/Beilstein_J_Org_Chem-12-16-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/87d8/4734429/ed5319ad5b1d/Beilstein_J_Org_Chem-12-16-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/87d8/4734429/e22433a07ac4/Beilstein_J_Org_Chem-12-16-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/87d8/4734429/9b1406f9c7c2/Beilstein_J_Org_Chem-12-16-g007.jpg

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本文引用的文献

1
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J Org Chem. 2015 Nov 6;80(21):11048-56. doi: 10.1021/acs.joc.5b02324. Epub 2015 Oct 26.
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Catalyst-controlled divergence in cycloisomerisation reactions of N-propargyl-N-vinyl sulfonamides: gold-catalysed synthesis of 2-sulfonylmethyl pyrroles and dihydropyridines.N-炔丙基-N-乙烯基磺酰胺环异构化反应中的催化剂控制的发散性:金催化合成2-磺酰基甲基吡咯和二氢吡啶。
Chem Commun (Camb). 2015 Sep 18;51(72):13748-51. doi: 10.1039/c5cc04871k. Epub 2015 Jul 10.
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