Abstract
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.
| Original language | English |
|---|---|
| Pages (from-to) | 168-176 |
| Number of pages | 9 |
| Journal | Advanced Synthesis and Catalysis |
| Volume | 357 |
| Issue number | 1 |
| DOIs | |
| Publication status | Published - 2015 Dec 4 |
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Keywords
- 2-arylquinazolines
- C-C bond formation
- Copper catalysts
- Isoindolo[1,2-a]quinazolines
- Rearrangement
ASJC Scopus subject areas
- Catalysis
- Organic Chemistry
Cite this
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. / Gawande, Sachin D.; Zanwar, Manoj R.; Kavala, Veerababurao; Kuo, Chun Wei; Rajawinslin, R. R.; Yao, Ching-Fa.
In: Advanced Synthesis and Catalysis, Vol. 357, No. 1, 04.12.2015, p. 168-176.Research output: Contribution to journal › Article
}
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
UR - http://www.scopus.com/inward/record.url?scp=84920726574&partnerID=8YFLogxK
UR - http://www.scopus.com/inward/citedby.url?scp=84920726574&partnerID=8YFLogxK
U2 - 10.1002/adsc.201400505
DO - 10.1002/adsc.201400505
M3 - Article
VL - 357
SP - 168
EP - 176
JO - Advanced Synthesis and Catalysis
JF - Advanced Synthesis and Catalysis
SN - 1615-4150
IS - 1
ER -