Synthesis of novel 2,2-disubstituted naphthodioxoles via an unprecedented reaction

Synthetic Utilization of α,β‐Chalcone Dibromide In Heterocyclic Chemistry and Stereoselective Debromination

“…In the view of this remarkable biological potential, Kapoor and co‐workers set forth a unprecedented and mild synthesis of several 2,2‐disubstituted naphthodioxoles 150 . α,β‐chalcone dibromide 2 when reacted with 2,3‐dihydroxynaphthalene 149 in presence of anhydrous K 2 CO 3 furnished 2,2‐disubstituted naphthodioxoles 150 through successive nucleophilic substitution reaction (Scheme ) …”

“…In the view of this remarkable biological potential, Kapoor and co-workers set forth a unprecedented and mild synthesis of several 2,2disubstituted naphthodioxoles 150. α,β-chalcone dibromide 2 when reacted with 2,3-dihydroxynaphthalene 149 in presence of anhydrous K 2 CO 3 furnished 2,2-disubstituted naphthodioxoles 150 through successive nucleophilic substitution reaction (Scheme 59). [146] Another application of α,β-chalcone dibromo-1-(4-fluoro-3-methylphenyl)-3-phenylpropanone and provided product 153 in regioselective manner (Scheme 60). [147] An expeditious synthesis of 5,6,8-triphenyl-5,10-dihydro [1,2,4]triazolo[5,1-b]quinazoline 155 by refluxing of α,β-chalcone dibromide 2 with 5-methyl-7-phenyl-4,7-dihydro-1,2,4triazolo[1,5-a]pyrimidine 154 for 5-7 minutes in presence CH 3 ONa/CH 3 OH has been reported by Lipson and co-workers (Scheme 61).…”