One‐pot Synthesis  of Highly Functionalized Pyrido‐1,3‐thiazin‐4‐ones Using Unprotected Sugars in a Task‐specific Ionic Liquid, [Bmim]SCN | Zendy

Rai Vijai K. | Zendy; Sharrof Vidya R. | Zendy

Premium

One‐pot Synthesis of Highly Functionalized Pyrido‐1,3‐thiazin‐4‐ones Using Unprotected Sugars in a Task‐specific Ionic Liquid, [Bmim]SCN

Author(s) -

Rai Vijai K.,

Sharrof Vidya R.

Publication year - 2017

Publication title -

journal of heterocyclic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 0.321

H-Index - 59

eISSN - 1943-5193

pISSN - 0022-152X

DOI - 10.1002/jhet.2690

Subject(s) - chemistry , ionic liquid , cascade , component (thermodynamics) , medicinal chemistry , combinatorial chemistry , organic chemistry , catalysis , chromatography , physics , thermodynamics

An original four‐component coupling strategy to iminosugar‐annulated 1,3‐thiazines, that is, pyrido‐1,3‐thiazin‐4‐ones using unprotected D‐xylose/D‐glucose, 2‐phenyl‐1,3‐oxazolan‐5‐one, [bmim]SCN, and NH4OAC/RNH2 is reported. The strategy involves a task‐specific ionic liquid, [bmim]SCN‐promoted cascade reactions involving hydrothiocyanation and aminoacetylative azaheterocyclization. The reactions give excellent yields (82‐95%) and are highly diastereoselective (>94%) in favor of cis isomer.

This content is not available in your region!

Continue researching here.

Having issues? You can contact us here

Accelerating Research