A facile and efficient synthesis of 2-amino-3-cyano-4H-chromenes and tetrahydrobenzo[b]pyrans using 2,2,2-trifluoroethanol as a metal-free and reusable medium

Screening of a library of 4-aryl/heteroaryl-4H-fused pyrans for xanthine oxidase inhibition: synthesis, biological evaluation and docking studies

“…In each occasion, the spectral data ( 1 H and 13 C NMR) of known compounds were compared with that reported in the literature. 6,7,-phenyl-4H-chromene-3-carbonitrile (1a) (Yu and Da-Ming, 2012;Xu et al, 2011), 2-amino-5,6,7,8-tetrahydro-4-(4-fluorophenyl)-5-oxo-4H-chromene-3-carbonitrile (1b) (Yu and Da-Ming, 2012), 2-amino-5,6,7,8-tetrahydro-4-(4-bromophenyl)-5-oxo-4H-chromene-3-carbonitrile (1c) (Yu and Da-Ming, 2012), 2-amino-5,6,7,8- (Xu et al, 2011), 2-amino-5,6,7,8-tetrahydro-4-(4-methoxyphenyl)-5-oxo-4H-chromene-3-carbonitrile (1i) (Xu et al, 2011;Rostamnia and Morsali, 2014), 2-amino-5,6,7,8-tetrahydro-4-(4-nitrophenyl)-5-oxo-4H-chromene-3-carbonitrile (1j) (Yu and Da-Ming, 2012;Xu et al, 2011;Rostamnia and Morsali, 2014;HosseiniMonfared et al, 2013), 2-amino-5,6,7,8-tetrahydro-4-(4-hydroxyphenyl)-5-oxo-4H-chromene-3-carbonitrile (1k) (Xu et al, 2011), 2-amino-5,6,7,8-tetrahydro-4-(furan-2-yl)-5-oxo-4H-chromene-3-carbonitrile (1m) (Xu et al, 2011), 2-amino-5,6,7,8-tetrahydro-4-(3,4-dimethoxyphenyl)-5-oxo-4H-chromene-3-carbonitrile (1q) (Yu and Da-Ming, 2012;Xu et al, 2011), 2-amino-5,6,7,8-tetrahydro-4-(4-chlorophenyl)-5-oxo-4H-chromene-3-carbonitrile (1s) (Yu and Da-Ming, 2012;Rostamnia and Morsali, 2014;HosseiniMonfared et al, 2013), 2-amino-5,6,7,8-tetrahydro-4-(3-nitrophenyl)-5-oxo-4H-chromene-3-carbonitrile (1v) (Xu et al, 2011), 2-amino-5,6,7,8-tetrahydro-7,7-dimethyl-5-oxo-4-phenyl-4H-chromene-3-carbonitrile (2a) (Kumar et al, 2009;Sadegh and Ali, 2014;Yu and Da-Ming, 2012;Gao et al, 2008;Hasaninejad et al, 2013;Jiang-Cheng et al, 2011;Bihani et al, 2013;Khaksar et al, 2012;Banerjee et al, 2011), 2-amino-5,6,7,8-tetrahydro-4-(4-fluorophenyl)-7,7-dimethyl-5-oxo-4H-chromene-3-carbonitrile (2b) …”

“…methoxyphenyl)-7,7-dimethyl-5-oxo-4H-chromene-3-carbonitrile (2h)(Yu and Da-Ming, 2012; Jiang-Cheng et al, 5-oxo-4H-chromene-3-carbonitrile (2i)(Kumar et al, 2009;Jiang-Cheng et al, 2011;Bihani et al, 2013;Khaksar et al, 2012;Banerjee et al, 2011), 2-amino-5,6,7,8-tetrahydro-4-(4-nitrophenyl)-7,7-dimethyl-5-oxo-4H-chromene-Fig. 4 a Binding poses of R-enantiomer (brown) and S-enantiomer (green) in binding cavity of XO.…”

Leucine: green and efficient catalyst for the synthesis of 4H-chromenes

“…Some derivatives of pyrans including chromenes exhibit wide range of biological activities [4], and possess molluscicidal [5], anticancer [6], antitubercular, anticoagulant, antiallergic, antibiotic, hypolipidemic, and immunomodulating properties [7]. These compounds are also industrially important as cosmetics, pigments and potentially biodegradable agrochemicals [8]. As a result, in recent years, much research activities in synthetic organic chemistry have been dedicated to the synthesis of 4H-chromenes due to their biological and pharmacological activities.…”

Green synthesis of 2-amino-7-hydroxy-4-aryl-4$H$-chromene-3-carbonitriles using ZnO nanoparticles prepared with mulberry leaf extract and ZnCl$_{2}$

“…Comparatively few methods have been described for the synthesis of 2-amino-7-hydroxy-4-aryl/alkyl-4H -chromene-3-carbonitriles applying the use of potassium phthalimide-N-oxyl, 18 2,2,2-trifluoroethanol, 19 Fe 3 O 4 -chitosan nanoparticles, 22 and MgO.…”