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Multi‐Component Reaction of 6‐Aminouracils, Aldehydes and Secondary Amines: Conversion of the Products into Pyrimido[4,5‐ d ]pyrimidines through C‐H Amination/Cyclization
Author(s) -
Borpatra Paran J.,
Rastogi Gaurav K.,
Saikia Ms. BS.,
Deb Mohit L.,
Baruah Pranjal K.
Publication year - 2019
Publication title -
chemistryselect
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.437
H-Index - 34
ISSN - 2365-6549
DOI - 10.1002/slct.201900210
Subject(s) - chemistry , aldehyde , amine gas treating , amination , acetic acid , organic chemistry , intramolecular force , solvent , catalysis , cascade reaction , ethanol , reductive amination , medicinal chemistry , combinatorial chemistry
Reaction of 6‐aminouracils with aldehydes and secondary amines catalyzed by acetic acid is reported here. This is in fact a domino aza‐Michael reaction. 6‐Aminouracil reacts first with aldehyde and then amine attacks the newly formed C=C bond, which is established from the mass spectral analysis of the reaction mixture. The products of the reaction are cyclized to pyrimido[4,5‐ d ]‐pyrimidines via intramolecular α‐C−H functionalization of tertiary amine promoted by I 2 ‐TBHP at room temperature in ethanol solvent. I 2 (10 mol %) and TBHP (1.5 eq.) are used for the cyclization reactions. Based on few controlled experiments a tentative radical mechanism is proposed for the cyclization step.