A cascade of acid-promoted C-O bond cleavage and redox reactions: from oxa-bridged benzazepines to benzazepinones.
A sequence of C-O bond cleavage and redox reactions in oxa-bridged azepines was realized under acid promoted conditions. This protocol provides an atom-economical and straightforward approach to access benzo[b]azepin-5(2H)-ones in high yields. The formal synthesis of tolvaptan was achieved by exploiting this new transformation.
The Center for Combinatorial Chemistry and Drug Discovery of Jilin University, The College of Chemistry and The School of Pharmaceutical Sciences, Jilin University, 1266 Fujin Lu, Changchun, Jilin 130021, P. R. China.
Yuewei
Y
Zhang
The Center for Combinatorial Chemistry and Drug Discovery of Jilin University, The College of Chemistry and The School of Pharmaceutical Sciences, Jilin University, 1266 Fujin Lu, Changchun, Jilin 130021, P. R. China.
Fengzhi
F
Yang
The Center for Combinatorial Chemistry and Drug Discovery of Jilin University, The College of Chemistry and The School of Pharmaceutical Sciences, Jilin University, 1266 Fujin Lu, Changchun, Jilin 130021, P. R. China.
Lianyou
L
Zheng
The Center for Combinatorial Chemistry and Drug Discovery of Jilin University, The College of Chemistry and The School of Pharmaceutical Sciences, Jilin University, 1266 Fujin Lu, Changchun, Jilin 130021, P. R. China.
Qun
Q
Dang
The Center for Combinatorial Chemistry and Drug Discovery of Jilin University, The College of Chemistry and The School of Pharmaceutical Sciences, Jilin University, 1266 Fujin Lu, Changchun, Jilin 130021, P. R. China.
Xu
X
Bai
D001381:Azepines / Q000138:chemical synthesis* / Q000737:chemistry; D001552:Benzazepines / Q000138:chemical synthesis / Q000737:chemistry*; D002384:Catalysis; D015394:Molecular Structure; D010084:Oxidation-Reduction; D010121:Oxytocin / Q000031:analogs & derivatives; D000077602:Tolvaptan
D001381:Azepines; D001552:Benzazepines; D000077602:Tolvaptan; D010121:Oxytocin; C015692:oxytocin, Asp(5)-