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由水杨酸和炔酸酯合成官能化苯并[1,3]二氧杂环丁烷-4-酮及其直接酰胺化反应

Synthesis of functionalized benzo[1,3]dioxin-4-ones from salicylic acid and acetylenic esters and their direct amidation.

作者信息

Bhaskaran Rasmi P, Nayak Kalinga H, Babu Beneesh P

机构信息

Department of Chemistry, National Institute of Technology Karnataka - NITK Surathkal 575025 Mangalore India

出版信息

RSC Adv. 2021 Jul 13;11(40):24570-24574. doi: 10.1039/d1ra05032j.

DOI:10.1039/d1ra05032j
PMID:35481005
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9036891/
Abstract

Direct synthesis of 4-benzo[][1,3]dioxin-4-one derivatives from salicylic acids and acetylenic esters (both mono- and disubstituted) has been described. The reaction is mediated by CuI and NaHCO in acetonitrile. Room temperature amidation of the synthesized 1,3-benzodioxinones with primary amines readily afforded the corresponding salicylamides in moderate to good yields.

摘要

已报道了由水杨酸和炔酸酯（单取代和双取代）直接合成4-苯并[][1,3]二氧杂环己二酮衍生物的方法。该反应由碘化亚铜和碳酸氢钠在乙腈中介导。合成的1,3-苯并二氧杂环己二酮与伯胺在室温下进行酰胺化反应，很容易以中等至良好的产率得到相应的水杨酰胺。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/67e9/9036891/84215f006c73/d1ra05032j-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/67e9/9036891/9b0a27a47d36/d1ra05032j-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/67e9/9036891/fbf1f9fbc202/d1ra05032j-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/67e9/9036891/84215f006c73/d1ra05032j-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/67e9/9036891/9b0a27a47d36/d1ra05032j-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/67e9/9036891/fbf1f9fbc202/d1ra05032j-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/67e9/9036891/84215f006c73/d1ra05032j-s2.jpg

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ACS Macro Lett. 2017 Dec 19;6(12):1392-1397. doi: 10.1021/acsmacrolett.7b00788. Epub 2017 Nov 30.
2
Catalyst-free synthesis of 3,1-benzoxathiin-4-ones/1,3-benzodioxin-4-ones.无催化剂合成3,1-苯并氧硫杂环戊烯-4-酮/1,3-苯并二恶英-4-酮。
Org Biomol Chem. 2021 Feb 25;19(7):1508-1513. doi: 10.1039/d0ob02543g.
3
Copper-catalyzed (4+1) and (3+2) cyclizations of iodonium ylides with alkynes.
铜催化的碘𬭩叶立德与炔烃的（4+1）和（3+2）环化反应。
Chem Commun (Camb). 2020 Sep 29;56(77):11429-11432. doi: 10.1039/d0cc04373g.
4
Highly efficient synthesis of benzodioxins with a 2-site quaternary carbon structure by secondary amine-catalyzed dual Michael cascade reactions.通过仲胺催化的双迈克尔级联反应高效合成具有 2 位季碳结构的苯并二氧杂环丁烷。
Org Biomol Chem. 2018 Aug 1;16(30):5533-5538. doi: 10.1039/c8ob01029c.
5
Divergent Synthesis of Quinolones and Dihydroepindolidiones via Cu(I)-Catalyzed Cyclization of Anilines with Alkynes.通过铜（I）催化的苯胺与炔烃的环化反应来实现喹诺酮和二氢表雄酮的发散合成。
Org Lett. 2018 Apr 6;20(7):1893-1897. doi: 10.1021/acs.orglett.8b00436. Epub 2018 Mar 20.
6
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8
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9
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J Org Chem. 2016 Feb 5;81(3):1047-56. doi: 10.1021/acs.joc.5b02602. Epub 2016 Jan 22.
10
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Acc Chem Res. 2015 Mar 17;48(3):628-42. doi: 10.1021/ar5004169. Epub 2015 Feb 17.