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

Sachin D. Gawande, Manoj R. Zanwar, Veerababurao Kavala, Chun Wei Kuo, R. R. Rajawinslin, Ching-Fa Yao

Research output: Contribution to journalArticle

13 Citations (Scopus)

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 languageEnglish
Pages (from-to)168-176
Number of pages9
JournalAdvanced Synthesis and Catalysis
Volume357
Issue number1
DOIs
Publication statusPublished - 2015 Dec 4

Fingerprint

Quinazolines
Isoindoles
Derivatives
Dimethyl sulfoxide
Dimethyl Sulfoxide
Amines
1,4-dioxane

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 journalArticle

Gawande, Sachin D. ; Zanwar, Manoj R. ; Kavala, Veerababurao ; Kuo, Chun Wei ; Rajawinslin, R. R. ; Yao, Ching-Fa. / 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. In: Advanced Synthesis and Catalysis. 2015 ; Vol. 357, No. 1. pp. 168-176.
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