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 | Zendy

Borpatra Paran J. | Zendy; Rastogi Gaurav K. | Zendy; Saikia Ms. BS. | Zendy; Deb Mohit L. | Zendy; Baruah Pranjal K. | Zendy

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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.

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