0000000001309953
AUTHOR
Nayana Joseph
An exclusive approach to 3,4-disubstituted cyclopentenes and alkylidene cyclopentenes via the palladium catalyzed ring opening of azabicyclic olefins with aryl halides
A simple and efficient method for the stereoselective ring opening of bicyclic hydrazines with various aryl halides under palladium catalysis has been elaborated. The reactions afforded trans-3,4-disubstituted cyclopentenes or alkylidene cyclopentenes in good to excellent yields. By taking advantage of multiple points of functionalization in the synthesized trans-3-phenyl-4-hydrazino-cyclopentene, we have synthesized the antidepressant Cypenamine (trans-2-phenylcyclopentylamine).
An easy access to fused chromanones via rhodium catalyzed oxidative coupling of salicylaldehydes with heterobicyclic olefins
Abstract Herein we describe a detailed study on the rhodium catalyzed oxidative coupling of salicylaldehydes with heterobicyclic olefins such as diazabicyclic olefins and urea-derived bicyclic olefins. The developed method provides an ideal route to fused chromanone systems in a single synthetic step. Moreover, the scope of this methodology was extended to different oxa/aza-bridged bicyclic urea derivatives.
An easy access to fused chromanones via rhodium catalyzed oxidative coupling of salicylaldehydes with heterobicyclic olefins
Herein we describe a detailed study on the rhodium catalyzed oxidative coupling of salicylaldehydes with heterobicyclic olefins such as diazabicyclic olefins and urea-derived bicyclic olefins. The developed method provides an ideal route to fused chromanone systems in a single synthetic step. Moreover, the scope of this methodology was extended to different oxa/aza-bridged bicyclic urea derivatives. peerReviewed
Rhodium catalyzed oxidative coupling of salicylaldehydes with diazabicyclic olefins: a one pot strategy involving aldehyde C–H cleavage and π-allyl chemistry towards the synthesis of fused ring chromanones
An efficient one pot strategy for the synthesis of cyclopentene fused chromanone derivatives through the direct oxidative coupling of salicylaldehydes with bicyclic olefins in the presence of a rhodium-copper catalyst system is described. This is the first report on the ring opening-ring closing of bicyclic hydrazines via metal catalyzed oxidative coupling reaction.
ChemInform Abstract: Rhodium Catalyzed Oxidative Coupling of Salicylaldehydes with Diazabicyclic Olefins: A One-Pot Strategy Involving Aldehyde C-H Cleavage and π-Allyl Chemistry Towards the Synthesis of Fused Ring Chromanones.
The title reaction involves the first example of ring opening and ring closing of bicyclic hydrazines (I) via metal catalyzed oxidative coupling reaction.
ChemInform Abstract: An Easy Access to Fused Chromanones via Rhodium Catalyzed Oxidative Coupling of Salicylaldehydes with Heterobicyclic Olefins.
Diazabicyclic and urea-derived bicyclic olefins react with salicylaldehydes to produce various types of fused chromanone systems of biological interest in a single step (mechanism).
CCDC 1449575: Experimental Crystal Structure Determination
Related Article: Ajesh Vijayan, T.V. Baiju, E. Jijy, Praveen Prakash, M. Shimi, Nayana Joseph, Petri M. Pihko, Sunil Varughese, K.V. Radhakrishnan|2016|Tetrahedron|72|4007|doi:10.1016/j.tet.2016.05.031
CCDC 782677: Experimental Crystal Structure Determination
Related Article: Nayana Joseph,Rani Rajan,Jubi John,N. V. Devika,S. Sarath Chand,E. Suresh,Petri M. Pihko,K. V. Radhakrishnan|2013|RSC Advances|3|7751|doi:10.1039/c3ra41504j