Double 1,3‐Dipolar Cycloaddition of 2,6‐Bis(arylmethylidene)cyclohexanones: A Novel Entry into the Synthesis of 2′,6′‐Bis‐spiro(1‐N‐Methyl‐4‐aryl‐pyrrolidine)cyclohexanones.

Abstract

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A Facile Solvent Free Claisen-Schmidt Reaction: Synthesis of α,α′-bis-(Substituted-benzylidene)cycloalkanones and α,α′-bis-(Substituted-alkylidene)cycloalkanones

“…Although studies on the Claisen-Schmidt reaction have been focused on α-alkylidene- and α-arylidene-carbonyl compounds, interest in α,α'-bisalkylidene- and α,α'-bisarylidene-carbonyl compounds is increasing. Particularly, α,α'- bis -(substituted-benzylidene)-cycloalkanones have been attracting much more attention, not only due to their intriguing biological activities such as antiangiogenic [ 7 , 8 ], quinine reductase inducer [ 9 ], arginine methyltransferase inhibitor [ 10 ], cytotoxicity [ 11 , 12 ], cholesterol-lowering activity [ 13 ], uses in agrochemicals, pharmaceuticals and perfumes [ 14 ], in bis -spiropyrrolidines [ 14 , 15 , 16 ], and as liquid crystalline polymer units [ 17 ], but also as important precursors for the synthesis of pyrimidine derivatives [ 18 ], 2,7-disubstituted tropones [ 19 ], and they are the synthetic intermediates of choice to functionalize the α, β-position during the total synthesis of natural products such as the cystodytins [ 20 ]. They have also been reported to possess drug resistance reversal properties [ 21 , 22 ].…”