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 | Zendy

Saikia Ujwal Pratim | Zendy; Borah Geetika | Zendy; Pahari Pallab | Zendy

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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.

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