Abstract
A series of 2-arylquinazolines have been synthesized in moderate to excellent yields by one-pot tandem reaction of (2-aminophenyl)methanols, aldehydes and ceric ammonium nitrate (CAN). The utility of this transformation was demonstrated by its compatibility with a wide range of functional groups. Thus, the method represents a simple and practical procedure to access 2-arylquinazolines.
Highlights
Quinazolines and derivatives thereof are ubiquitous structural motifs that frequently occur in a wide variety of bioactive natural products such as prazosin [1], lapatinib [2], icotinib [3], etc
They possess a wide range of biological and pharmacological activities, including antibacterial [4], anti-inflammatory [5], antiplasmodial [6], antitumor [7], antimicrobial and antioxidant properties [8]. They have been used as photochemotherapeutic agents [9], DNA-gyrase, JAK2, PDE5, and EGFR tyrosine kinase inhibitors [10] as well as CB2 receptor agonists [11]
Yang reported that substituted quinazolines possess novel potent and selective FLT3 inhibitory and anti-acute myeloid leukemia activities [12]
Summary
Quinazolines and derivatives thereof are ubiquitous structural motifs that frequently occur in a wide variety of bioactive natural products such as prazosin [1], lapatinib [2], icotinib [3], etc They possess a wide range of biological and pharmacological activities, including antibacterial [4], anti-inflammatory [5], antiplasmodial [6], antitumor [7], antimicrobial and antioxidant properties [8]. The condensation reactions of 2-aminobenzylamines with aldehydes followed by subsequent oxidation with strong oxidants (e.g., 2,3-dichloro-5,6-dicyano-l,4-benzoquinone (DDQ) [21], MnO2 [22], and NaClO [23]) provide a conventional but simple method to synthesize quinazolines (Scheme 1(a)). We wish to report a new method for the synthesis of quinazolines by using a one-pot tandem reaction of (2-aminophenyl)methanols, aldehydes and ceric ammonium nitrate (CAN) (Scheme 1(b))
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