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One‐Pot Synthesis of 2‐Arylquinazolines and Tetracyclic Isoindolo[1,2‐ a ]quinazolines via Cyanation Followed by Rearrangement of ortho ‐Substituted 2‐Halo‐ N ‐arylbenzamides
Author(s) -
Gawande Sachin D.,
Zanwar Manoj R.,
Kavala Veerababurao,
Kuo ChunWei,
Rajawinslin R. R.,
Yao ChingFa
Publication year - 2015
Publication title -
advanced synthesis and catalysis
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.541
H-Index - 155
eISSN - 1615-4169
pISSN - 1615-4150
DOI - 10.1002/adsc.201400505
Subject(s) - chemistry , isoindole , cyanation , solvent , quinazoline , yield (engineering) , medicinal chemistry , amine gas treating , organic chemistry , catalysis , materials science , metallurgy
The one‐pot synthesis of substituted 2‐arylquinazoline derivatives and tetracylic isoindolo[1,2‐ a ]quinazoline via cyanation followed by rearrangement of ortho ‐substituted 2‐halo‐ N ‐arylbenzamides is described. Using dimethyl sulfoxide (DMSO) as the solvent, the cleavage of the tetracyclic isoindole fused quinazoline leads to the formation of 2‐arylquinazoline derivatives. When 1,4‐dioxane is used as the solvent, tetracyclic isoindole fused quinazolines are produced in good yield. A wide range of products, including 2‐phenylquinazolin‐4‐amine, 4‐methyl‐2‐phenylquinazoline and long‐chain 2‐phenyl‐4‐styrylquinazoline derivatives were produced in moderate to good yields using DMSO as the solvent. However, various tetracyclic isoindole fused quinazoline derivatives were obtained in good yields when 1,4‐dioxane was used as the solvent.