Azide‐Induced Furan Ring Opening for the Synthesis of Functionalized Indoles

Azide‐Induced Furan Ring Opening for the Synthesis of Functionalized Indoles Научная публикация

Журнал

Asian Journal of Organic Chemistry
ISSN: 2193-5815 , E-ISSN: 2193-5807

Вых. Данные

Год: 2024, Том: 13, Номер: 12, Номер статьи : e202400373, Страниц : DOI: 10.1002/ajoc.202400373

Авторы

Chalikidi Petrakis N. ¹ , Magkoev Taimuraz T. ¹ , Egorov Dmitry I. ¹ , Kolodina Alexandra A. ² , Uchuskin Maxim G. ³ , Trushkov Igor V. ⁴ , Abaev Vladimir ^1,5

Организации

1	North-Ossetian State University Chemico-technological department, 43-46 Vatutina str. 362025 Vladikavkaz RUSSIAN FEDERATION
2	Institute of Physical and Organic Chemistry, Southern Federal University, 194/2 Stachka St., Rostov on Don, 344090 Russian Federation
3	Perm State University Department of chemistry RUSSIAN FEDERATION
4	Zelinsky Institute of Organic Chemistry RAS Laboratory of Directed Functionalisation of Organic Molecular Systems RUSSIAN FEDERATION
5	North Caucasus Federal University, 1a Pushkin st., Stavropol, 355009 Russian Federation

We investigated the reactivity of various furans towards 2-azidobenzaldehydes, heterocyclic azidoaldehydes, and substituted 2-azidobenzyl alcohols to synthesize 2-(2-azidobenzyl)furan derivatives, revealing the azide group's remarkable compatibility with typical Friedel-Crafts reaction conditions. Additionally, we demonstrated that these derivatives could be efficiently synthesized via a diazotization/azidation sequence from 2-(2-aminobenzyl)furans containing electron-donating substituents, successfully avoiding undesirable side reactions. Furthermore, we developed a synthetic methodology for preparing 2-(2-acylvinyl)indoles, involving the thermal generation of nitrenes to initiate furan ring opening. Notably, our approach utilizes the azidoaryl group and the furan ring separated by a saturated carbon atom that distinguishes it from known indole syntheses in which these moieties are conjugated. The broad applicability and high efficiency of our method, using readily available starting materials, highlight its potential as a versatile synthetic tool.

Chalikidi P.N. , Magkoev T.T. , Egorov D.I. , Kolodina A.A. , Uchuskin M.G. , Trushkov I.V. , Abaev V.
Azide‐Induced Furan Ring Opening for the Synthesis of Functionalized Indoles
Asian Journal of Organic Chemistry. 2024. V.13. N12. e202400373 . DOI: 10.1002/ajoc.202400373 WOS Scopus OpenAlex

Web of science:	WOS:001354423600001
Scopus:	2-s2.0-85208435920
OpenAlex:	W4402967001

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