Synthesis, X-ray structure and NMR data of 12-amino-15-phenyl-2,5,8-trioxa-13-azabicyclo[9.2.2]pentadeca-1(14),12- diene-11,14-dicarbonitrile

Abstract

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A New Multicomponent Synthetic Route to Hexahydropyrido[2,3‐d]pyrimidine Derivatives

“…Refluxing benzaldehyde (1 equiv) and excess malononitrile (2 equiv) under the same reaction conditions gave the expected 2‐amino‐6‐ethoxy‐4‐phenylpyridine‐3,5‐dicarbonitrile 4 as reported in the literatures , while excess benzaldehyde (2 equiv) and one equivalent of malononitrile only gave 2‐benzylidenemalononitrile A as the intermediate. In the light of these observations, the reaction presumably proceeds by the following pathway (Scheme ).…”

“…One‐pot three‐component condensation reaction of substituted benzaldehydes, malononitrile, and thiophenol or ethanol in a 1:2.2:1 molar ratio in the presence of different catalysts such as K 2 CO 3 , NaHCO 3 , NaOH , NaH , Et 3 N , DBU , DABCO , piperidine , TBAF , TBAH , [bmim]OH , H 3 BO 3 , ZnCl 2 , MgO , Ce‐V/Al 2 O 3 , KF/Al 2 O 3 , ZrOCl 2 .8H 2 O/NaNH 2 , basic alumina , silica NPs , CaO NPs , CuI NPs , and ZnO NPs for the synthesis of polysubstituted pyridines has already been reported. Surprisingly, when we reacted equimolar amounts of malononitrile and benzaldehydes in ethanol under mild basic conditions, various hexahydropyrido[2,3‐ d ]pyrimidines 3a – h were obtained in good to excellent yield through a pseudo‐five‐component reaction (Scheme ).…”

Reusable Ce‐V Loaded Alumina Catalyst for Multicomponent Synthesis of Substituted Pyridines in Green Media

“…Within a long‐term research program aimed at developing pharmaceutically active materials, synthesis of substituted pyridines are of special implication because of varied biological activities such as anticancer , antimicrobial , antibacterial , antifungal , anti‐inflammatory , antioxidant activity , cytotoxicity , and anti‐HIV . Thus, the synthesis of polysubstituted pyridine derivatives have fascinated many researchers, and several approaches have been pursued using catalysts, such as K 2 CO 3 , NaH , Et 3 N , [bmIm]OH , ZnCl 2 , DBU , MgO , KF/Al 2 O 3 , H 3 BO 3 , and NaOH .…”