Transposition of Aromaticity from a Furan to a Cyclohexane Ring in Furoisoindoles During the Interaction of 3-(Furyl)allylamines with Bromomaleic Anhydride

Autor:	Svetlana M. Eroshkina, Eugeniya V. Nikitina, Khidmet S. Shikhaliev, Kseniia A. Alekseeva, Fedor I. Zubkov, Elizaveta A. Kvyatkovskaya, Vladimir P. Zaytsev, Hieu H. Truong, Victor N. Khrustalev
Rok vydání:	2020
Předmět:	Isoindoles 010405 organic chemistry Chemistry Organic Chemistry Aromaticity 010402 general chemistry Ring (chemistry) 01 natural sciences Medicinal chemistry 0104 chemical sciences chemistry.chemical_compound Furan Dehydrohalogenation Moiety Isoindole Diels–Alder reaction
Zdroj:	Synlett. 31:255-260
ISSN:	1437-2096 0936-5214
Popis:	An unexpected four-step reaction sequence was discovered in the course of investigation of the interaction between 3-(furan-2-yl)allylamines and bromomaleic anhydride. This conversion begins with the initial N-acylation of the allylamines by the anhydride, followed by intramolecular Diels–Alder reaction, which is accompanied by a dehydrohalogenation, and ends with the formation of partially unsaturated furo[2,3-f]isoindoles followed by transposition of aromaticity from the furan moiety to the neighboring cyclohexane ring. The reaction between 3-(furan-3-yl)allylamines and bromomaleic anhydride does not stop at a furo[2,3-f]isoindole formation step, but proceeds further with the cleavage of the furan ring in a 100% atom-efficient fashion to provide polysubstituted isoindoline-4-carboxylic acids.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::2fe53ba67e72bc54a6a7ac6958ee6436 https://doi.org/10.1055/s-0039-1690782 Zobrazit plný text záznamu