Abstract
A simple approach to synthesize 4b,5,6,9-tetrahydro-7H-dibenzo[c,e]pyrrolo[1,2-a]azepin- 7-one has been developed, based on a three-step transformation of 2-(2-bromophenyl)cyclopropane-1,1-diester. The key stage in this method is an intramolecular cross-coupling of 1-(2-bromobenzyl)-5-(2-bromophenyl)pyrrolidin-2-one under continuous flow conditions in an H-Сube-Pro using commercially available supported Pd catalysts.
Highlights
Dibenz[c,e]azepine derivatives attract the attention of synthetic and medicinal chemists due to their potential use in human and veterinary medicine
Title compound 1 was synthesized from readily available dimethyl 2-(2-bromophenyl)-cyclopropaneTitle
The facile three-step sequence, including a cyclopropane ring opening with an azide ion, accompanied by decarboxylation, a Staudinger/aza-Wittig domino reaction combined with the reductive cyclization, and an intramolecular cross-coupling reaction of 1-(2-bromobenzyl)-5-(2bromophenyl)pyrrolidin-2-one, provides a concise route to 4b,5,6,9-tetrahydro-7H-dibenzo[c, e]pyrrolo[1,2-a]azepin-7-one
Summary
Dibenz[c,e]azepine derivatives attract the attention of synthetic and medicinal chemists due to their potential use in human and veterinary medicine. As a part of our efforts towards the synthesis of N-containing heterocycles of potential pharmacological value based on the donor-acceptor cyclopropane transformations [30,31,32,33,34,35], we have recently described a convenient synthesis of polyoxygenated tetrahydrodibenzo[c,e]pyrrolo[1,2-a]azepines [35]. This protocol included: (1) Cyclopropane ring opening with an azide ion, followed by in situ Krapcho dealkoxycarbonylation; (2) the phosphine-mediated reaction of the obtained 4-aryl-4-azidobutyrate with aromatic aldehydes and subsequent in situ reductive cyclization of the formed imine, yielding.
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