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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.