Preparation of 9H-Tribenzazepine and Its 1-Methoxy Derivative

DOI: 10.1021/jo00012a023

Source and publish data:

Journal of Organic Chemistry p. 3906 - 3908 (1991)

Update date:2022-08-04

Topics:

Authors:

Axtell, Holly C.

Howell, William M.

Schmid, Lawrence G.

Cann, Michael C.

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Article abstract of DOI:10.1021/jo00012a023

Two convenient routes to 9H-tribenzazepine (2) have been developed.The first method involves the deoxygenation and hydrolysis of 1,4-dihydro-1,4-epoxy-9-acetyl-9H-tribenzazepine (8) employing low-valent titanium.The second method employs the reactive intermediate 10,11-didehydro-5-acetyl-5H-dibenzazepine (7) in a Diels-Alder reaction with 1,3-cyclohexadiene.The resulting cycloadduct 13 upon undergoing a retro-Diels-Alder reaction and hydrolysis yields 2. 1-Methoxy-9H-tribenzazepine (11) was prepared from ring opening of 8 to1-hydroxy-9-acetyl-9H-tribenzazepine (10) followed by methylation with dimethylsulfate and hydrolysis.

Full text of DOI:10.1021/jo00012a023

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