Investigation of the synthesis and analgesic activity of 1??substituted 4??(propananilido) perhydroazepines

…, S Andurkar, TN Riley, DE Walters…

Index: De Ruiter; Andurkar; Riley; Walters; Noggle Jr. Journal of Heterocyclic Chemistry, 1992 , vol. 29, # 4 p. 779 - 786

Full Text: HTML

Citation Number: 6

Abstract

Abstract Methods are explored to enhance the efficiency and versatility of the synthesis of the 1-substituted 4-(propananilido) perhydroazepine analgesics. The modified synthesis begins with ring expansion of 1-carbethoxy-4-piperidinone 3 with ethyl diazoacetate and boron trifluoride to yield 1, 5-biscarbethoxyperhydroazepin-4-one 4. Selective hydrolysis of 4 followed by decarboxylation provides 1-carbethoxyperhydroazepin-4-one 6. Reductive ...