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Synthesis of Isoindolo[2,1‐ a ]quinazoline‐5,11‐dione Derivatives via the Reductive One‐Pot Reaction of N ‐Substituted 2‐Nitrobenzamides and 2‐Formylbenzoic Acids
Author(s) -
Mahdavi Mohammad,
Najafi Ramin,
Saeedi Mina,
Alipour Eskandar,
Shafiee Abbas,
Foroumadi Alireza
Publication year - 2013
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.201200199
Subject(s) - chemistry , nitro , nucleophile , medicinal chemistry , quinazoline , nucleophilic substitution , ring (chemistry) , stereochemistry , organic chemistry , catalysis , alkyl
Various isoindolo[2,1‐ a ]quinazoline‐5,11‐dione derivatives 3 were synthesized in good yields by means of the reductive reaction of N ‐substituted 2‐nitrobenzamides 1 and 2‐formylbenzoic acids 2 in the presence of SnCl 2 ⋅2 H 2 O under reflux in EtOH ( Scheme, Table ). The procedure needed two steps, the reduction of the nitro group of the 2‐nitrobenzamide and ring closure by nucleophilic addition of the NH 2 group to both the formyl and carboxylic acid CO groups.