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Abstract
In an effort to provide a green synthetic route for heterocyclic scaffolds, new macro analogs of acyclic Mannich derivatives have been synthesized in good yields in a one-pot, efficient fashion. The acyclic symmetrical and unsymmetrical 2-[(E)-(benzylideneamino)(aryl)methyl]cyclododecanones have been synthesized by condensation of cyclododecanone, aromatic aldehyde, and ammonium acetate in ethanolic media. By infrared, NMR, and mass spectral analyses, their structures were determined. Examination of crystal structure of a p-Cl and o-Br analogs reveals the minimum energy [3333] square conformation of cyclododecanone ring. In the crystal, molecules aggregate in dimeric subunits formed by C-Cl … π and C-H..π interactions. The reported one-pot, multichain reaction of macrocycles is the first synthetic attempt of acyclic compounds in this type of Mannich reaction involving ketones containing active methylene groups.
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GRAPHICAL ABSTRACT
ACKNOWLEDGMENTS
N. S. K. thanks the Council of Scientific and Industrial Research (CSIR), New Delhi, for the Senior research fellowship. R. S. R. acknowledges CSIR for funding under the scientist's pool scheme.
Notes
Note: where
; parameters a and b are 0.0701, 0.3657 (4c), and 0.0651, 0.000 (4g), respectively.
The current affiliation for N.S.K. is Center for Plastic Information Systems (CPIS), Department of Chemistry Education, Pusan National University, Pusan, South Korea.