Synthesis of a-substituted 2-(1H-1,2,4-triazol-3-yl)acetates and 5-amino-2,4-dihydro-3H-pyrazol-3-ones via the Pinner strategy

TETRAHEDRON LETTERS

卷:69

Article

Khomenko, Dmytro M.^1,2  Doroshchuk, Roman O.^1,2  Ivanova, Hanna, V²  Zakharchenko, Borys, V²  Raspertova, Ilona, V²  Vaschenko, Oleksandr V.²  Shova, Sergiu³  Dobrydnev, Alexey, V^1,2  Moroz, Yurii S.^2,4  Grygorenko, Oleksandr O.^1,2  Lampeka, Rostyslav D.² 

[1] Enamine Ltd, Chervonotkatska St 78, UA-02094 Kiev, Ukraine

[2] Taras Shevchenko Natl Univ Kyiv, Volodymyrska St 60, UA-01601 Kiev, Ukraine

[3] Petro Poni Inst Macromol Chem, Aleea Gr Ghica Voda 41A, Iasi 700487, Romania

[4] Chemspace, Ilukstes Iela 38-5, LV-1082 Riga, Latvia

关键词: Cyclization;    Nitrogen heterocycles;    Imidates;    Spiro compounds;    Azoles;   

DOI  :  10.1016/j.tetlet.2021.152956

来源: Elsevier

【 摘 要 】

A series of 2-(1H-1,2,4-triazol-3-yl)acetates, as well as 4-mono- and 4,4-disubstituted 5-amino-2,4-dihydro-3H-pyrazol-3-ones (including spirocyclic derivatives) have been synthesized using the Pinner reaction strategy. alpha-Mono- and alpha,alpha-disubstituted ethyl cyanoacetates were converted into the corresponding carboxyimidate salts that served as the key intermediates. Their further reaction with formylhydrazide or hydrazine hydrate provided triazolylacetates or aminopyrazolones (including spirocyclic derivatives), depending on the structure of the starting Pinner salt and the nature of the nucleophile. The scope and limitations of the developed synthetic method have been established. (C) 2021 Elsevier Ltd. All rights reserved.

【 授权许可】

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