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在无溶剂钙(II)催化下,胺引发的高简便氧化苯并环化反应合成邻氨基苯甲酸酯

Amine-Triggered Highly Facile Oxidative Benzannulation Reaction for the Synthesis of Anthranilates under Solvent-Free Calcium(II) Catalysis.

作者信息

Yaragorla Srinivasarao, Dada Ravikrishna

机构信息

School of Chemistry, University of Hyderabad, P.O. Central University, Gachibowli, Hyderabad, Telangana 500046, India.

School of Chemical Sciences and Pharmacy, Central University of Rajasthan, Bandersindri, Kishangarh, Rajasthan 305817, India.

出版信息

ACS Omega. 2017 Aug 23;2(8):4859-4869. doi: 10.1021/acsomega.7b00753. eCollection 2017 Aug 31.

DOI:10.1021/acsomega.7b00753
PMID:31457765
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC6641687/
Abstract

An amine-triggered facile synthetic approach of anthranilates has been described through benzannulation of readily available chemicals under one-pot solvent-free conditions using Ca(OTf) as the sustainable catalyst. In this regioselective approach, we described a reasonably longer cascade, which proceeds through β-enamino ester formation/Michael addition/intramolecular aldol reaction/elimination/aromatization/oxidative debenzylation/lactonization with a broad substrate scope and high yields. The isolation of intermediates authenticated the mechanism, and the synthetic utility of the products was also demonstrated.

摘要

通过使用Ca(OTf)作为可持续催化剂,在无溶剂的一锅法条件下,对易于获得的化学品进行苯并环化反应,描述了一种胺引发的邻氨基苯甲酸酯的简便合成方法。在这种区域选择性方法中,我们描述了一个相对较长的串联反应,该反应通过β-烯胺酯形成/迈克尔加成/分子内羟醛反应/消除/芳构化/氧化脱苄基/内酯化进行,具有广泛的底物范围和高产率。中间体的分离证实了反应机理,并且还展示了产物的合成效用。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c40a/6641687/f3a269df0ae6/ao-2017-00753r_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c40a/6641687/0fcc55438169/ao-2017-00753r_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c40a/6641687/d9bf77307393/ao-2017-00753r_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c40a/6641687/0d5564896abb/ao-2017-00753r_0008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c40a/6641687/f3a269df0ae6/ao-2017-00753r_0004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c40a/6641687/0fcc55438169/ao-2017-00753r_0006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c40a/6641687/d9bf77307393/ao-2017-00753r_0005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c40a/6641687/0d5564896abb/ao-2017-00753r_0008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c40a/6641687/f3a269df0ae6/ao-2017-00753r_0004.jpg

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