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一锅法在水相中由 PPh-NBS 促进的五元及六元稠合二氢吡啶的多米诺合成。

One-pot domino synthesis of five- and six-membered fused dihydropyridines promoted by PPh-NBS in aqueous medium.

机构信息

Fluoro & Agrochemicals Department, CSIR-Indian Institute of Chemical Technology, Tarnaka, Hyderabad, 500 007, India.

Academy of Scientific and Innovative Research (AcSIR), Ghaziabad, Uttar Pradesh, 201002, India.

出版信息

Org Biomol Chem. 2023 May 31;21(21):4434-4439. doi: 10.1039/d3ob00472d.

Abstract

A facile one-pot synthesis of five- and six-membered fused dihydropyridines such as chromenodihydropyridines, pyrazolodihydropyridines and isoxazolopyridines was accomplished for the first time by employing PPh-NBS a formal [3 + 2 + 1] cycloaddition of 1,3-bisnucleophiles (, 2-aminochromone, 4-aminochromone, 5-aminopyrazole and 5-aminoisoxazole), β-enaminones and aldehydes in aqueous medium. The present approach involves a Michael type addition followed by intramolecular cyclization leading to the formation of two new C-C bonds and one C-N bond. High compatibility and excellent yields are the advantages of this protocol.

摘要

首次通过使用 PPh-NBS,实现了在水介质中 1,3-双亲核试剂( 、2-氨基色酮、4-氨基色酮、5-氨基吡唑和 5-氨基异恶唑)、β-烯胺酮和醛的[3+2+1]形式的正环加成,简便地一锅合成了五元及六元稠合二氢吡啶,如色烯二氢吡啶、吡唑并二氢吡啶和异恶唑并吡啶。该方法涉及迈克尔型加成,然后进行分子内环化,形成两个新的 C-C 键和一个 C-N 键。该方案的优点是具有高兼容性和优异的收率。

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