BIOMAT Database Logo BIOMAT Database Logo

Facile access to C-substituted piperazin-2-ones and mianserin derivative enabled by chemoselective carbene insertion and cyclization cascade. 2024

Dharmendra Kumar, and Urmila Unnikrishnan, and Malleswara Rao Kuram
Medicinal and Process Chemistry Division, CSIR-Central Drug Research Institute, Lucknow 226031, India. malleswara.kuram@cdri.res.in.

The chemoselective N-H insertion of unsymmetrical diamines into carbene is a longstanding challenge. A simple copper-catalyzed strategy for synthesizing C-substituted piperazinones is described, employing easily accessible diazo compounds and 1,2-diamines. The reaction proceeded via chemo-selective carbene insertion at the comparatively less nucleophilic amine, followed by instantaneous cyclization. The protocol was further extended to access NH-free piperazinone, and the synthesis of a Mianserin derivative.

UI MeSH Term Description Entries

Related Publications

Dharmendra Kumar, and Urmila Unnikrishnan, and Malleswara Rao Kuram
Cascade coupling/cyclization process to N-substituted 1,3-dihydrobenzimidazol-2-ones.
October 2007, Organic letters,
Dharmendra Kumar, and Urmila Unnikrishnan, and Malleswara Rao Kuram
Radical cascade silylation/cyclization of 1,7-dienes to access silyl-substituted benzo[b]azepin-2-ones.
March 2024, Chemical communications (Cambridge, England),
Dharmendra Kumar, and Urmila Unnikrishnan, and Malleswara Rao Kuram
Facile access to 2-hydroxy-2-substituted indole-3-ones via a copper-catalyzed oxidative cyclization of 2-arylethynylanilines.
June 2023, Chemical communications (Cambridge, England),
Dharmendra Kumar, and Urmila Unnikrishnan, and Malleswara Rao Kuram
Stereoselective Cyclization Cascade of Dihydroquinoxalinones by Visible-Light Photocatalysis: Access to the Polycyclic Quinoxalin-2(1H)-ones.
July 2022, Organic letters,
Dharmendra Kumar, and Urmila Unnikrishnan, and Malleswara Rao Kuram
Cyclization by catalytic ruthenium carbene insertion into C(sp³)-H bonds.
January 2012, Angewandte Chemie (International ed. in English),
Dharmendra Kumar, and Urmila Unnikrishnan, and Malleswara Rao Kuram
A new and facile synthetic approach to substituted 2-thioxoquinazolin-4-ones by the annulation of a pyrimidine derivative.
November 2010, Beilstein journal of organic chemistry,
Dharmendra Kumar, and Urmila Unnikrishnan, and Malleswara Rao Kuram
NaOH-Promoted Chemoselective Cascade Cyclization of Cyclopropyl Esters with Unsaturated Imines: Access to Bioactive Cyclopenta[c]pyridine Derivatives.
September 2019, Organic letters,
Dharmendra Kumar, and Urmila Unnikrishnan, and Malleswara Rao Kuram
I2/TBHP-Mediated tandem cyclization and oxidation reaction: Facile access to 2-substituted thiazoles and benzothiazoles.
January 2019, Organic & biomolecular chemistry,
Dharmendra Kumar, and Urmila Unnikrishnan, and Malleswara Rao Kuram
Electro-Triggered Cascade Cyclization to Access Phosphinyl-Substituted N-Containing Heterocycles.
February 2023, The Journal of organic chemistry,
Dharmendra Kumar, and Urmila Unnikrishnan, and Malleswara Rao Kuram
Facile synthesis of 2-iodo-spiro[indene-1,1'-isobenzofuran]-3'-ones via iodine-promoted cascade cyclization.
November 2012, Chemical communications (Cambridge, England),
Copied contents to your clipboard!