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 |
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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 |
Keywords
- 2-arylquinazolines
- C-C bond formation
- Copper catalysts
- Isoindolo[1,2-a]quinazolines
- Rearrangement
ASJC Scopus subject areas
- Catalysis
- Organic Chemistry
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CCDC 993227: Experimental Crystal Structure Determination
Gawande, S. D. (Creator), Zanwar, M. R. (Creator), Kavala, V. (Creator), Kuo, C.-W. (Creator), Rajawinslin, R. R. (Creator) & Yao, C.-F. (Creator), Cambridge Crystallographic Data Centre, 2015
DOI: 10.5517/cc12bjlj, http://www.ccdc.cam.ac.uk/services/structure_request?id=doi:10.5517/cc12bjlj&sid=DataCite
Dataset