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Lewis‐Acid‐Catalysed Activation of Nitriles: A Microwave‐Assisted Solvent‐Free Synthesis of 2,4‐Disubstituted Quinazolines and 1,3‐Diazaspiro[5.5]undec‐1‐enes
Author(s) -
Saikia Ujwal Pratim,
Borah Geetika,
Pahari Pallab
Publication year - 2018
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.201701585
Subject(s) - chemistry , quinazolinone , amidine , catalysis , lewis acids and bases , microwave irradiation , lewis acid catalysis , intramolecular force , solvent , organic chemistry , medicinal chemistry , combinatorial chemistry
Two different modes of cyclization take place to synthesize quinazoline, quinazolinone, and 1,3‐diazaspiro[5.5]undec‐1‐ene derivatives through the Lewis‐acid‐catalysed activation of both aliphatic and aromatic nitriles in a single‐step, solvent‐free, and transition‐metal‐free reaction. An amidine is expected to form as an intermediate; this then undergoes intramolecular cyclization in a one‐pot reaction sequence. The reaction is carried out under microwave irradiation using trimethylsilyltrifluoromethane sulfonate (TMSOTf) as a catalyst and nitriles as a nitrogen source with the respective reaction partners.