Unusual Highly Diastereoselective Rh(II)-catalyzed Dimerization of Diazo Arylidene Succinimides Provides Access to New Dibenzazulene Scaffold

Submitting author affiliation:
Saint Petersburg State University, Peterhof, Russian Federation

Beilstein Arch. 2022, 202217. https://doi.org/10.3762/bxiv.2022.17.v1

Published 21 Mar 2022

cc-by Logo


Formation of unusual unsymmetrical dimers or/and indenes via Rh2(esp)2-catalyzed decomposition of diazo arylidene succinimides has been investigated. The reaction proceeded under mild conditions, and its result was shown to strongly depend on the nature of the substituents in the diazo substrate. The new reaction provides access to dibenzoazulenodipyrrole and indenopyrrole derivatives in moderate to high yield. Dibenzoazulenodipyrroles bearing alkyl substituents at the nitrogen atom showed pronounced cytotoxocity against A549 human lung adenocarcinoma cell line while N-aryl analogs were non-cytotoxic.

Keywords: 3-diazo-2-arylidene succinimides; rhodium carbene; cyclopropanation; 1,5-C‒C bond migration

Supporting Information

Format: PDF Size: 4.3 MB   Download

How to Cite

When a peer-reviewed version of this preprint is available, this information will be updated in the information box above. If no peer-reviewed version is available, please cite this preprint using the following information:

Vepreva, A.; Bunev, A. S.; Kudinov, A. Y.; Kantin, G.; Krasavin, M.; Dar'in, D. Beilstein Arch. 2022, 202217. doi:10.3762/bxiv.2022.17.v1

Download Citation

Citation data can be downloaded as file using the "Download" button or used for copy/paste from the text window below.
Citation data in RIS format can be imported by all major citation management software, including EndNote, ProCite, RefWorks, and Zotero.