title: Beyond the Five and Six: Evaluation of Seven-Membered Cyclic Anhydrides in the Castagnoli-Cushman Reaction.
abstract: The Castagnoli-Cushman reaction with benzo[d]oxepine-2,4(1H,5H)-dione as an anhydride component allowed for preparation of 2,3-disubstituted 4-oxo-2,3,4,5-tetrahydro-1H-benzo[d]azepine-1-carboxylic acids in 21-75% yields and with good trans diastereoselectivity. The method worked with imines generated from aromatic or α-branched aliphatic aldehydes and is amenable for both parallel synthesis and scale-up. The procedure for epimerization of the resulting trans-disubstituted tetrahydrobenzo[d]azepines to their cis isomers was also developed.
authors.affiliation: National Taras Shevchenko University of Kyiv , Volodymyrska Street 64, Kyiv 01601, Ukraine.
authors.forename: Mykhailo I
authors.initials: MI
authors.lastname: Adamovskyi
authors.affiliation: National Taras Shevchenko University of Kyiv , Volodymyrska Street 64, Kyiv 01601, Ukraine.
authors.forename: Sergey V
authors.identifier: 0000-0003-4281-8268
authors.initials: SV
authors.lastname: Ryabukhin
authors.affiliation: Institute of Organic Chemistry, National Academy of Sciences of Ukraine , Murmanska Street 5, Kyiv 02660, Ukraine.
authors.forename: Dmitriy A
authors.initials: DA
authors.lastname: Sibgatulin
authors.affiliation: Institute of Organic Chemistry, National Academy of Sciences of Ukraine , Murmanska Street 5, Kyiv 02660, Ukraine.
authors.forename: Eduard
authors.initials: E
authors.lastname: Rusanov
authors.affiliation: National Taras Shevchenko University of Kyiv , Volodymyrska Street 64, Kyiv 01601, Ukraine.
authors.forename: Oleksandr O
authors.initials: OO
authors.lastname: Grygorenko