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Synthesis 2014; 46(12): 1613-1620
DOI: 10.1055/s-0033-1341105
DOI: 10.1055/s-0033-1341105
paper
One-Pot Chemoselective Synthesis of 2,4,6,8-Tetrasubstituted Quinazolines via Microwave-Assisted Consecutive Bis-SNAr/Bis-Suzuki–Miyaura Cross-Coupling Reactions
Further Information
Publication History
Received: 14 January 2014
Accepted after revision: 13 March 2014
Publication Date:
02 April 2014 (online)
Abstract
A practical and efficient synthesis of 2,4,6,8-tetrasubstituted quinazolines through one-pot chemoselective sequential bis-SNAr/bis-Suzuki–Miyaura reactions under microwave irradiation is presented. The bis-SNAr reaction occurs selectively at the C-2 and C-4 positions of 6,8-dibromo-2,4-dichloroquinazoline and the bis-Suzuki–Miyaura cross-coupling at C-6 and C-8. This procedure affords convergent synthesis of polysubstituted quinazoline derivatives in high yields in very few steps and tolerates a wide range of boronic acids and amines.
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