Concise synthesis of 12a-methyl-11-aryl-1,2-dihydrobenzo[f]pyrrolo[1,2-a]quinolin-3(12aH)-ones as racemic 14-azaestrogen analogs

• Published in: Steroids Vol. 98; pp. 107 - 113
• Main Authors: Abdelkhalik, Ashraf M., Paul, Nawal K., Jha, Amitabh
• Format: Journal Article
• Language: English
• Published: United States Elsevier Inc 01-06-2015
• Subjects: 12a-Methyl-11-aryl-1,2-dihydrobenzo[f]pyrrolo[1,2-a]quinolin-3(12aH)-ones; 14-Azasteroids; Aza Compounds - chemical synthesis; Aza Compounds - chemistry; Domino reaction; Estrogen analogs; Estrogens - chemical synthesis; Estrogens - chemistry; Gold (III) catalysis; Gold (III) catalysis; 12a-Methyl-11-aryl-1,2-dihydrobenzo[f]pyrrolo[1,2-a]quinolin-3(12aH)-ones; 14-Azasteroids; Estrogen analogs; Domino reaction
• ISSN: 0039-128X; 1878-5867
• DOI: 10.1016/j.steroids.2015.03.010

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•A series of 14-azasteroids were synthesized as azaestrogen analogs.•The synthesis was achieved in three steps from commonly available starting materials.•The key reaction step involved one CN and two CC bond formation in tandem.•The key reaction step was catalyzed by AuBr3/AgSbF6 catalyst system.
A concise method for the synthesis of 14-azasteroid analogs with angular methyl group at C-13 of the steroidal nucleus has been reported in this paper. We have developed an interesting cascade reaction of arylacetylenes and N-(naphthalen-2-yl)pent-4-ynamides under gold (III)-catalysis to produce novel tetracyclic 12a-methyl-11-aryl-1,2-dihydrobenzo[f]pyrrolo[1,2-a]quinolin-3(12aH)-ones which may be viewed as 14-azaestrogen analogs.