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PO/TfOH介导的胺与二酸的多米诺缩合环化反应：在无催化剂和无溶剂条件下合成吲哚里西啶生物碱的一条途径。

PO/TfOH mediated domino condensation-cyclization of amines with diacids: a route to indolizidine alkaloids under catalyst- and solvent-free conditions.

作者信息

Mandrekar Ketan S, Tilve Santosh G

机构信息

School of Chemical Sciences, Goa University Taleigao Goa 403206 India

出版信息

RSC Adv. 2022 Jun 15;12(28):17701-17705. doi: 10.1039/d2ra02534e. eCollection 2022 Jun 14.

DOI:10.1039/d2ra02534e
PMID:35765320
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC9200442/
Abstract

A domino condensation-cyclization method is developed to synthesize indolizidine alkaloids using a PO/TfOH reagent system without the employment of either a catalyst or solvent. The use of a few aliphatic and aromatic dicarboxylic acids is shown along with various primary amines. This method is suitable for synthesizing pyrrolo[2,1-]isoquinolines, pyrido[2,1-]isoquinolines, and isoindolo[1,2-]isoquinolinones in excellent yields. When phthalic acid is used, a workup with either NaBH or a saturated NaHCO solution provided 12-H or 12-OH isoindolo[1,2-]isoquinolinones, respectively.

摘要

开发了一种多米诺缩合环化方法，使用PO/TfOH试剂体系合成吲哚里西啶生物碱，无需使用催化剂或溶剂。展示了几种脂肪族和芳香族二羧酸与各种伯胺的使用情况。该方法适用于以优异的产率合成吡咯并[2,1-]异喹啉、吡啶并[2,1-]异喹啉和异吲哚并[1,2-]异喹啉酮。当使用邻苯二甲酸时，分别用NaBH或饱和NaHCO溶液后处理，可得到12-H或12-OH异吲哚并[1,2-]异喹啉酮。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/c517/9200442/4e36a7d729d2/d2ra02534e-s8.jpg
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