TY - JOUR
T1 - 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
AU - Gawande, Sachin D.
AU - Zanwar, Manoj R.
AU - Kavala, Veerababurao
AU - Kuo, Chun Wei
AU - Rajawinslin, R. R.
AU - Yao, Ching-Fa
PY - 2015/12/4
Y1 - 2015/12/4
N2 - 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.
AB - 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.
KW - 2-arylquinazolines
KW - C-C bond formation
KW - Copper catalysts
KW - Isoindolo[1,2-a]quinazolines
KW - Rearrangement
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U2 - 10.1002/adsc.201400505
DO - 10.1002/adsc.201400505
M3 - Article
AN - SCOPUS:84920726574
VL - 357
SP - 168
EP - 176
JO - Advanced Synthesis and Catalysis
JF - Advanced Synthesis and Catalysis
SN - 1615-4150
IS - 1
ER -