Expeditious synthesis of 5,6,7 ,8-tetrahydro-imidazo[1,2-a ] pyrimidin-2-ones and 3,4,6,7 ,8,9-hexahydro-pyrimido[,2-a ] pyrimidin-2-ones

A convenient synthesis of new 5,6,7 ,8-tetrahydro-imidazo[ 1,2-a]pyrimidin-2-ones and 3,4,6,7 ,8,9-hexahydro-pyrimido[1 ,2a]pyrimidin-2- ones from the Baylis-Hillman adducts of acrylonitrile and their derivatives is described. A common strategy employed to achieve the syntheses of title compounds involved generation of diamines from different Baylis-Hillman derivatives followed by treatment with cyanogen bromide at reflux temperature to trigger a double intramolecular cyclization.

Sodium hydride-mediated cascade reaction towards the synthesis of 1,5-disubstituted uracil from cyanamides derived from the Baylis-Hillman ad-ducts

Sodium hydride-mediated cascade reaction towards the synthesis of 1,5-disubstituted uracil from cyanamides derived from the Baylis-Hillman ad-ducts

A facile route to the synthesis of novel 2-amino-1,4,5,6-tetrahydropyrimidines from Baylis-Hillman products of acrylonitrile

A facile route for the synthesis of novel 5-substituted-2-amino-1,4,5,6-tetrahydro pyrimidines from the Baylis-Hillman adducts obtained from reaction of aldehydes and acrylonitrile is described.

Studies toward the construction of substituted piperidine-2-ones and pyridine-2-ones from Baylis-Hillman adducts: Discovery of a facile synthesis of 5-methyl-4-oxo-6-aryl-3-aza-bicyclo[3.1.0]hexane-1-carboxylates

Studies toward the construction of functionalised piperidone derivatives from derivatives of Baylis-Hillman adducts are described. Interestingly the 6-oxo-4-aryl-piperidine-3-carboxylates generated during the study serve as precursor for the facile synthesis of 4-oxo-6-aryl-3-aza-bicyclo[3.1.0]hexane-1-carboxylates

A Facile synthesis of 3-Methylene-4-aryl-1,3,4,5-tetrahydro-benzo[b][1,4] di-azepin-2-ones and 3-arylemethylene-4,5-dihydro-3H-benzo[b][1,4]diazepin-2-ylamines

A simple and convenient synthesis of 3-methylene-4-aryl-1,3,4,5-tetrahydro-benzo[b][1,4] diazepin-2-ones was accomplished by the SN2 nucleophilic substitution of the acetates of Baylis-Hillman adducts of acrylate with 1,2-phenylenediamines followed by base-mediated intramolecular cyclization. On the other hand similar substrates derived from the Baylis-Hillman adducts of acrylonitrile via Pinner’s reaction leads to 3-arylmethylene-4,5-dihydro-3H-benzo[b][1,4]diazepin-2-ylamines in good yields..

Application of primary allyl amines afforded by the Baylis-Hillman adducts for heterocyclic synthesis: Generation of 5-benzyl-4(3H)-pyrimidinones and 2-benzylidene-2,3-dihydro-pyrrolizin-1-ones

The applications of the primary allyl amines afforded by the acetyl derivative of Baylis-Hillman adducts of acrylate for the synthesis of heterocycles using robust reactions are described. In the first strategy a one-pot synthesis of 5-benzyl-4(3H)-pyrimidinones have been achieved via N-formylation of the amines in the presence of neat formamide followed by ammonium formate-mediated cyclization. These pyrimidinones have been demonstrated to be excellent precursor to the 4-pyridinamine derivatives. In the second strategy the synthesis of 2-benzylidene-2,3-dihydro-pyrrolizin-1-ones have been accomplished via treatment of allyl amine with dimethoxyfuran followed by saponification and PPA-mediated intramolecular cyclization.