An efficient approach to isoindolo[2,1-b][2]benzazepines via intramolecular [4+2] cycloaddition of maleic anhydride to 4-α-furyl-4-N-benzylaminobut-1-enes

Autor:	K. F. Turchin, Alexey V. Varlamov, Fedor I. Zubkov, Ekaterina V. Boltukhina
Rok vydání:	2004
Předmět:	Stereochemistry Organic Chemistry Aromatization Maleic anhydride Alkylation Biochemistry Cycloaddition Benzazepine Acylation chemistry.chemical_compound chemistry Furan Intramolecular force Drug Discovery
Zdroj:	Tetrahedron. 60:8455-8463
ISSN:	0040-4020
Popis:	Acylation of 4-α-furyl-4- N -benzylaminobut-1-enes with maleic anhydride gave 4-oxo-3-aza-10-oxatricyclo[5.2.1.0 1,5 ]dec-8-ene-6-carboxylic acid via amide formation followed by intramolecular Diels–Alder reaction of furan (IMDAF). The cycloaddition proceeded under mild reaction conditions (25 °C) and provided only the exo -adduct in quantitative yield. Treatment of this compound with PPA gave isoindolo[2,1- b ][2]benzazepine derivatives via ring opening, aromatization and intramolecular electrophilic alkylation. In order to extend the scope of the reaction sequence, 7-oxo-5,11b,12,13-tetrahydro-7 H -isoindolo[2,1- b ][2]benzazepine-8-carboxylic acids were further transformed into useful synthetic intermediates.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::baacd810327f861a75d52a0226800c26 https://doi.org/10.1016/j.tet.2004.07.008 Zobrazit plný text záznamu Full Text from ScienceDirect