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新型吡嗪并吲哚酮的高度区域选择性和非对映选择性合成——一种碱介导的乌吉-烷基化序列

Highly regioselective and diastereoselective synthesis of novel pyrazinoindolones a base-mediated Ugi--alkylation sequence.

作者信息

Tajik Maryam, Shiri Morteza, Hussain Faiq H S, Lotfi Nosood Yazdanbakhsh, Baeiszadeh Behnaz, Amini Zahra, Bikas Rahman, Pyra Anna

机构信息

Department of Organic Chemistry, Faculty of Chemistry, Alzahra University Vanak Tehran 1993893973 Iran

Medical Analysis Department, Applied Science Faculty, Tishk International University Erbil Kurdistan Region Iraq.

出版信息

RSC Adv. 2023 Jun 6;13(25):16963-16969. doi: 10.1039/d3ra02065g. eCollection 2023 Jun 5.

DOI:10.1039/d3ra02065g
PMID:37288378
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC10243185/
Abstract

An efficient base-mediated/metal-free approach has been developed for the synthesis of 1-oxo-1,2,3,4-tetrahydropyrazino[1,2-]indole-3-carboxamide derivatives intramolecular indole N-H alkylation of novel bis-amide Ugi-adducts. In this protocol the Ugi reaction of ()-cinnamaldehyde derivatives, 2-chloroaniline, indole-2-carboxylic acid and different isocyanides was designed for the preparation of bis-amides. The main highlight of this study is the practical and highly regioselective preparation of new polycyclic functionalized pyrazino derivatives. This system is facilitated by NaCO mediation in DMSO and 100 °C conditions.

摘要

已开发出一种高效的碱介导/无金属方法,用于合成1-氧代-1,2,3,4-四氢吡嗪并[1,2-]吲哚-3-甲酰胺衍生物,该方法通过新型双酰胺Ugi加合物的分子内吲哚N-H烷基化反应实现。在该方案中,设计了()-肉桂醛衍生物、2-氯苯胺、吲哚-2-羧酸和不同异腈的Ugi反应来制备双酰胺。本研究的主要亮点是新型多环官能化吡嗪衍生物的实用且高度区域选择性的制备。该体系在二甲基亚砜中由碳酸钠介导并在100℃条件下进行。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1ba9/10243185/679c25d2d003/d3ra02065g-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1ba9/10243185/783955572d5f/d3ra02065g-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1ba9/10243185/2c64c617e2d3/d3ra02065g-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1ba9/10243185/79fe0c68c5c9/d3ra02065g-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1ba9/10243185/dcff96cd4b11/d3ra02065g-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1ba9/10243185/679c25d2d003/d3ra02065g-s2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1ba9/10243185/783955572d5f/d3ra02065g-f1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1ba9/10243185/2c64c617e2d3/d3ra02065g-s1.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1ba9/10243185/79fe0c68c5c9/d3ra02065g-f2.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1ba9/10243185/dcff96cd4b11/d3ra02065g-f3.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1ba9/10243185/679c25d2d003/d3ra02065g-s2.jpg

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Synthesis and Biological Activities of Pyrazino[1,2-]indole and Pyrazino[1,2-]indol-1-one Derivatives.吡嗪并[1,2 - ]吲哚及吡嗪并[1,2 - ]吲哚 - 1 - 酮衍生物的合成与生物活性
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