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以4-芳基-2-丙炔酸、二芳基碘鎓盐、四丁基溴化铵和亚硫酸钠一锅法制备4-芳基-3-溴香豆素

One-pot preparation of 4-aryl-3-bromocoumarins from 4-aryl-2-propynoic acids with diaryliodonium salts, TBAB, and NaSO.

作者信息

Sasaki Teppei, Moriyama Katsuhiko, Togo Hideo

机构信息

Department of Chemistry, Graduate School of Science, Chiba University, Yayoi-cho 1-33, Inage-ku, Chiba 263-8522, Japan.

Molecular Chirality Research Center, Chiba University, Yayoi-cho 1-33, Inage-ku, Chiba 263-8522, Japan.

出版信息

Beilstein J Org Chem. 2018 Feb 5;14:345-353. doi: 10.3762/bjoc.14.22. eCollection 2018.

DOI:10.3762/bjoc.14.22
PMID:29507639
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC5815302/
Abstract

Various 4-aryl-3-bromocoumarins were smoothly obtained in moderate yields in one pot by treating 3-aryl-2-propynoic acids with diaryliodonium triflates and KCO in the presence of CuCl, followed by the reaction with tetrabutylammonium bromide (TBAB) and NaSO. The obtained 3-bromo-4-phenylcoumarin was transformed into 4-phenylcoumarin derivatives bearing C-H, C-S, C-N, and C-C bonds at 3-position.

摘要

通过在氯化铜存在下，用双芳基三氟甲磺酸碘鎓盐和碳酸钾处理3-芳基-2-丙炔酸，然后与四丁基溴化铵（TBAB）和亚硫酸钠反应，一锅法以中等产率顺利得到了各种4-芳基-3-溴香豆素。所得到的3-溴-4-苯基香豆素被转化为在3-位带有C-H、C-S、C-N和C-C键的4-苯基香豆素衍生物。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e059/5815302/0af0f43cb2e2/Beilstein_J_Org_Chem-14-345-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e059/5815302/91f3f1aaa6df/Beilstein_J_Org_Chem-14-345-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e059/5815302/43b4603573fb/Beilstein_J_Org_Chem-14-345-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e059/5815302/07fe9e9bf912/Beilstein_J_Org_Chem-14-345-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e059/5815302/4fa711579eaf/Beilstein_J_Org_Chem-14-345-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e059/5815302/0af0f43cb2e2/Beilstein_J_Org_Chem-14-345-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e059/5815302/91f3f1aaa6df/Beilstein_J_Org_Chem-14-345-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e059/5815302/43b4603573fb/Beilstein_J_Org_Chem-14-345-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e059/5815302/07fe9e9bf912/Beilstein_J_Org_Chem-14-345-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e059/5815302/4fa711579eaf/Beilstein_J_Org_Chem-14-345-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/e059/5815302/0af0f43cb2e2/Beilstein_J_Org_Chem-14-345-g006.jpg

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Chemistry. 2017 Nov 13;23(63):15852-15863. doi: 10.1002/chem.201702732. Epub 2017 Sep 1.
3
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5
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