p-TSA 催化 5-氨基吡唑和 3°/2°-丙炔醇的 6-endo-trig/dig 环化反应：获得吡唑并[1,5-a]二氢嘧啶和吡唑并[3,4-b]吡啶。

IF 2.9 3区化学 Q1 CHEMISTRY, ORGANIC

Organic & Biomolecular Chemistry Pub Date : 2024-10-02 DOI:10.1039/d4ob01255k

Nagaraju Medishetti , Bhanu Prasad Banda , Krishnaiah Atmakur

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引用次数: 0

摘要

在对-TSA 的存在下，利用 5-氨基吡唑、3°/2°-丙炔醇和炔酮，简便、直接地合成了融合的吡唑并[1,5-a]二氢嘧啶和吡唑并[3,4-b]吡啶。该反应通过 5-aminopyrazoles 的异戊烯化（N-烷基化）/丙炔化（C-烷基化）进行，然后进行分子内 6-endo-trig/dig 环化，生成新的 C-N 和 C-C 键，最终得到标题产物。该方法具有反应条件简单、试剂价格低廉、产率较高和克级合成等优点。

本文章由计算机程序翻译，如有差异，请以英文原文为准。

p-TSA catalyzed 6-endo-trig/dig cyclization of 5-aminopyrazoles and 3°/2°-propargylic alcohols: access to pyrazolo[1,5-a]dihydropyrimidines and pyrazolo[3,4-b]pyridines†

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p-TSA catalyzed 6-endo-trig/dig cyclization of 5-aminopyrazoles and 3°/2°-propargylic alcohols: access to pyrazolo[1,5-a]dihydropyrimidines and pyrazolo[3,4-b]pyridines†

A facile, straightforward synthesis of fused pyrazolo[1,5-a]dihydropyrimidines and pyrazolo[3,4-b]pyridines is accomplished by using 5-aminopyrazoles, 3°/2°-propargylic alcohols and ynones in the presence of p-TSA. The reaction proceeds through allenylation (N-alkylation)/propargylation (C-alkylation) of 5-aminopyrazoles, followed by intramolecular 6-endo-trig/dig cyclization leading to the title products with the formation of new C–N and C–C bonds. Operationally simple reaction conditions, inexpensive reagents, better yields, and gram-scale synthesis are the advantages of this protocol.

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来源期刊

Organic & Biomolecular Chemistry 化学-有机化学

CiteScore

5.50

自引率

9.40%

发文量

1056

审稿时长

1.3 months

期刊介绍： Organic & Biomolecular Chemistry is an international journal using integrated research in chemistry-organic chemistry. Founded in 2003 by the Royal Society of Chemistry, the journal is published in Semimonthly issues and has been indexed by SCIE, a leading international database. The journal focuses on the key research and cutting-edge progress in the field of chemistry-organic chemistry, publishes and reports the research results in this field in a timely manner, and is committed to becoming a window and platform for rapid academic exchanges among peers in this field. The journal's impact factor in 2023 is 2.9, and its CiteScore is 5.5.