Display options
Cite
Dwivedi V, Rajesh M, Kumar R, et al. A stereoselective thiocyanate conjugate addition to electron deficient alkynes and concomitant cyclization to N,S-heterocycles. Chem Commun (Camb). 2017;53(80):11060-11063doi: 10.1039/c7cc06081e.
Dwivedi, V., Rajesh, M., Kumar, R., Kant, R., & Sridhar Reddy, M. (2017). A stereoselective thiocyanate conjugate addition to electron deficient alkynes and concomitant cyclization to N,S-heterocycles. Chemical communications (Cambridge, England), 53(80), 11060-11063. https://doi.org/10.1039/c7cc06081e
Dwivedi, Vikas, et al. "A stereoselective thiocyanate conjugate addition to electron deficient alkynes and concomitant cyclization to N,S-heterocycles." Chemical communications (Cambridge, England) vol. 53,80 (2017): 11060-11063. doi: https://doi.org/10.1039/c7cc06081e
Dwivedi V, Rajesh M, Kumar R, Kant R, Sridhar Reddy M. A stereoselective thiocyanate conjugate addition to electron deficient alkynes and concomitant cyclization to N,S-heterocycles. Chem Commun (Camb). 2017 Oct 05;53(80):11060-11063. doi: 10.1039/c7cc06081e. PMID: 28948277.
Copy Download .nbib Format: NLM
Share it on

Chem Commun (Camb). 2017 Oct 05;53(80):11060-11063. doi: 10.1039/c7cc06081e.

A stereoselective thiocyanate conjugate addition to electron deficient alkynes and concomitant cyclization to N,S-heterocycles.

Chemical communications (Cambridge, England)

Vikas Dwivedi, Manda Rajesh, Ravi Kumar, Ruchir Kant, Maddi Sridhar Reddy

Affiliations

  1. Medicinal & Process Chemistry Division, CSIR-Central Drug Research Institute, BS-10/1, Sector 10, Jankipuram Extension, Sitapur Road, Lucknow 226031, India.

PMID: 28948277 DOI: 10.1039/c7cc06081e

Abstract

A regio- and stereoselective thiocyanate addition to ynones is achieved using KSCN in AcOH at 70 °C. The reaction is extendable to ynals, ynesulfones, ynoic acids and ynoates. Adducts from ynones were readily transformed into thiazine-2-thione derivatives under slightly modified reaction conditions. In contrast, thiocyanated adducts from ynamides underwent an in situ decyanative amido cyclization towards isothiazolones. None of these events needed any transition metal or catalyst, attaining a high synthetic value.

Publication Types