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Azoalkene chemistry provides practical access to 5-aminopyrazoles selectively protected at the N-1 position Научная публикация

Журнал Tetrahedron Letters
ISSN: 0040-4039 , E-ISSN: 1873-3581
Вых. Данные Год: 2026, Том: 178, Номер статьи : 155987, Страниц : DOI: 10.1016/j.tetlet.2026.155987
Авторы Kokuev Aleksandr O. 1 , Sukhorukov Alexey Yu. 1
Организации
1 Laboratory of Organic and Metal−Organic Nitrogen−Oxygen Systems (LOMONOS), N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky prosp. 47, Moscow 119991, Russian Federation

Реферат: 5-Aminopyrazoles are extensively used as building blocks in medicinal chemistry. However, selective protection of endo- and exocyclic nitrogen atoms is challenging. Here, we describe a convenient protocol for the synthesis of 1-Boc-protected 5-aminopyrazoles through Michael addition of cyanide to azoalkenes followed by spontaneous cyclization of the resulting α-cyanohydrazones. The process utilizes readily available α-halohydrazones, acetone cyanohydrin as a safer substitute for cyanide, and aqueous DMSO as the reaction medium. The method enables further synthetic diversification of the resulting 1-Boc-5-aminopyrazoles through reactions with electrophilic agents.
Библиографическая ссылка: Kokuev A.O. , Sukhorukov A.Y.
Azoalkene chemistry provides practical access to 5-aminopyrazoles selectively protected at the N-1 position
Tetrahedron Letters. 2026. V.178. 155987 . DOI: 10.1016/j.tetlet.2026.155987 WOS Scopus OpenAlex
Даты:
Поступила в редакцию: 5 дек. 2025 г.
Опубликована online: 6 февр. 2026 г.
Идентификаторы БД:
Web of science: WOS:001686950400001
Scopus: 2-s2.0-105029418407
OpenAlex: W7126379577
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