Journal
SYNTHESIS-STUTTGART
Volume 49, Issue 11, Pages 2535-2543Publisher
GEORG THIEME VERLAG KG
DOI: 10.1055/s-0036-1588727
Keywords
copper; 2-halobenzimidamides; sodium azide; catalysis; 4-aminoquinazolines
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Funding
- National Natural Science Foundation of China [81602957]
- Natural Science Foundation of Jiangsu Province, China [BK20161035]
- Universities Natural Science Research Project of Jiangsu Province [15KJB350002]
- Nanjing Medical University Education Development Foundation [2014NJMUZD019]
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A highly efficient copper-catalyzed one-pot protocol is developed for the synthesis of 4-aminoquinazolines from easily available 2-iodo- or 2-bromobenzimidamides, aldehydes, and sodium azide. This one-pot approach proceeds via consecutive copper-catalyzed SNAr substitution, reduction, cyclization, oxidation and tautomerization. The corresponding target products (26 examples) are obtained in 50-90% yield.
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