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间歇和连续流动条件下光催化合成异色满酮和异苯并呋喃酮

Photocatalyzed synthesis of isochromanones and isobenzofuranones under batch and flow conditions.

作者信息

Anselmo Manuel, Moni Lisa, Ismail Hossny, Comoretto Davide, Riva Renata, Basso Andrea

机构信息

Università degli Studi di Genova, Dipartimento di Chimica e Chimica Industriale, Via Dodecaneso 31, Genova, Italy.

出版信息

Beilstein J Org Chem. 2017 Jul 25;13:1456-1462. doi: 10.3762/bjoc.13.143. eCollection 2017.

DOI:10.3762/bjoc.13.143
PMID:28845188
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC5550801/
Abstract

Photocatalyzed reactions of 2-(alkoxycarbonyl)benzenediazonium tetrafluoroborates with various alkenes afforded isochromanones in good yields, according to a mechanism that was investigated. The advantage of using highly soluble esters rather than carboxylic acids as starting compounds became evident when the reactions were performed under flow conditions. On the other hand, when 2-vinylbenzoic acid derivatives were employed as reagents, isobenzofuranones were obtained together with unprecedented benzo[][1,3]oxazepin-1(5)-ones, with the latter derived from incorporation of the solvent (acetonitrile).

摘要

据研究的机理，2 -（烷氧羰基）苯重氮四氟硼酸盐与各种烯烃的光催化反应能以良好产率得到异色满酮。当反应在流动条件下进行时，使用高溶解性的酯而非羧酸作为起始化合物的优势变得明显。另一方面，当使用2 -乙烯基苯甲酸衍生物作为试剂时，会同时得到异苯并呋喃酮以及前所未有的苯并[][1,3]恶唑嗪 - 1(5) - 酮，后者是由溶剂（乙腈）掺入而产生的。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dfe9/5550801/32eca0d96275/Beilstein_J_Org_Chem-13-1456-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dfe9/5550801/17196ff5c6e7/Beilstein_J_Org_Chem-13-1456-g004.jpg
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https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dfe9/5550801/3cae51bae3f9/Beilstein_J_Org_Chem-13-1456-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dfe9/5550801/406d09765362/Beilstein_J_Org_Chem-13-1456-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dfe9/5550801/3d1b166ac358/Beilstein_J_Org_Chem-13-1456-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dfe9/5550801/391fbd8638a8/Beilstein_J_Org_Chem-13-1456-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dfe9/5550801/24a8750cccaa/Beilstein_J_Org_Chem-13-1456-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dfe9/5550801/c8427eed2bb8/Beilstein_J_Org_Chem-13-1456-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dfe9/5550801/32eca0d96275/Beilstein_J_Org_Chem-13-1456-g010.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dfe9/5550801/17196ff5c6e7/Beilstein_J_Org_Chem-13-1456-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dfe9/5550801/4ceb397cd76a/Beilstein_J_Org_Chem-13-1456-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dfe9/5550801/3cae51bae3f9/Beilstein_J_Org_Chem-13-1456-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dfe9/5550801/406d09765362/Beilstein_J_Org_Chem-13-1456-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dfe9/5550801/3d1b166ac358/Beilstein_J_Org_Chem-13-1456-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dfe9/5550801/391fbd8638a8/Beilstein_J_Org_Chem-13-1456-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dfe9/5550801/24a8750cccaa/Beilstein_J_Org_Chem-13-1456-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dfe9/5550801/c8427eed2bb8/Beilstein_J_Org_Chem-13-1456-g009.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/dfe9/5550801/32eca0d96275/Beilstein_J_Org_Chem-13-1456-g010.jpg

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