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Synthesis 2016; 48(22): 3976-3984
DOI: 10.1055/s-0035-1562504
DOI: 10.1055/s-0035-1562504
paper
Palladium-Catalyzed Cross-Coupling of 4-Tosyloxyquinazolines with Organoindium Reagents: An Efficient Route to 4-Substituted Quinazolines
Further Information
Publication History
Received: 04 April 2016
Accepted after revision: 26 May 2016
Publication Date:
25 July 2016 (online)
Abstract
An efficient route to 4-substituted quinazolines by arylation or alkylation of quinazolinones under mild conditions is described. 4-Tosyloxyquinazolines were obtained through the reaction of quinazolinones and p-methylbenzenesulfonyl chloride in the presence of K2CO3. The cross-coupling reaction of 4-tosyloxyquinazolines with organoindium reagents, carried out in tetrahydrofuran, catalyzed by Pd2(dba)3/ (2-furyl)3P led to the formation of 4-functionalized quinazolines in good to excellent yields. Higher yields were obtained by the one-pot reaction of quinazolinone, p-methylbenzenesulfonyl chloride, Pd2(dba)3-/(2-furyl)3P, and organoindium reagent. These methods using organoindium compounds as coupling partners provided an efficient route to 4-(hetero)aryl/alkylquinazolines, especially 4-substituted quinazolines bearing a halogen scaffold.
Key words
quinazoline - organoindium reagent - 4-tosyloxyquinazoline - 4-substituted quinazoline - cross-couplingSupporting Information
- Supporting information for this article is available online at http://dx.doi.org/10.1055/s-0035-1562504.
- Supporting Information
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