TY - JOUR

T1 - Tricyclic 2-benzazepines obtainedviaan unexpected cyclization involving nitrilium ylides

AU - Inyutina, Anna

AU - Dar'in, Dmitry

AU - Kantin, Grigory

AU - Krasavin, Mikhail

N1 - Funding Information: We are grateful to the Russian Science Foundation for financial support (grant #20-13-00024). We thank the Research Centre for Magnetic Resonance, the Center for Chemical Analysis and Materials Research, and the Centre for X-ray Diffraction Methods of Saint Petersburg State University Research Park for obtaining the analytical data. Publisher Copyright: © The Royal Society of Chemistry 2021.

PY - 2021/6/21

Y1 - 2021/6/21

N2 - Attempted use of (E)-3-arylidene-4-diazopyrrolidine-2,5-diones in the Rh(ii)-catalyzed condensation with nitriles to form 1,3-oxazoles led to an unexpected outcome. The nitrilium ylide species thought to form on Rh(ii)-catalyzed decomposition of diazo compounds underwent a cyclization onto the nearby arylidene moiety followed by 1,5-hydride shift. This led to the formation of a 2-benzazepine core which has special significance for drug discovery and can be considered a privileged scaffold.

AB - Attempted use of (E)-3-arylidene-4-diazopyrrolidine-2,5-diones in the Rh(ii)-catalyzed condensation with nitriles to form 1,3-oxazoles led to an unexpected outcome. The nitrilium ylide species thought to form on Rh(ii)-catalyzed decomposition of diazo compounds underwent a cyclization onto the nearby arylidene moiety followed by 1,5-hydride shift. This led to the formation of a 2-benzazepine core which has special significance for drug discovery and can be considered a privileged scaffold.

UR - http://www.scopus.com/inward/record.url?scp=85108093428&partnerID=8YFLogxK

U2 - 10.1039/d1ob00773d

DO - 10.1039/d1ob00773d

M3 - Article

C2 - 34027962

AN - SCOPUS:85108093428

VL - 19

SP - 5068

EP - 5071

JO - Organic and Biomolecular Chemistry

JF - Organic and Biomolecular Chemistry

SN - 1477-0520

IS - 23

ER -