One-pot Synthesis of Highly Functionalized Pyrido-1,3-thiazin-4-ones Using Unprotected Sugars in a Task-specific Ionic Liquid, [Bmim]SCN
Corresponding Author
Vijai K. Rai
Department of Chemistry, Guru Ghasidas Vishwavidyalaya, Bilaspur, Chhattisgarh, 495 009 India
E-mail: [email protected]Search for more papers by this authorVidya R. Sharrof
Department of Chemistry, Guru Ghasidas Vishwavidyalaya, Bilaspur, Chhattisgarh, 495 009 India
Search for more papers by this authorCorresponding Author
Vijai K. Rai
Department of Chemistry, Guru Ghasidas Vishwavidyalaya, Bilaspur, Chhattisgarh, 495 009 India
E-mail: [email protected]Search for more papers by this authorVidya R. Sharrof
Department of Chemistry, Guru Ghasidas Vishwavidyalaya, Bilaspur, Chhattisgarh, 495 009 India
Search for more papers by this authorAbstract
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.
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