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mediate B. Then attack by an amine at the carbonyl centre of
activated amide intermediate B generates another intermedi-
ate C. Subsequent rearrangement to D, and finally elimination
of ammonia yields the desired transamidation product by
regenerating the chitosan catalyst.
In conclusion, we have developed a novel chitosan-catalyzed
transamidation protocol for selective transamination in an
efficient manner. Compared to known transamidation catalysts,
chitosan is inexpensive, readily available, and recyclable without
any loss of catalytic activity and with quantitative yields. A wide
range of benzylic, aromatic, aliphatic, propargylic, hetero-
aromatic and secondary amines can be effectively used to
produce the corresponding transamidation products in good to
excellent yields. Under similar conditions benzo[d]thiazole,
benzo[d]-oxazole and 1H-benzo[d]imidazole were obtained in a
one-pot transamidation of formamide with aminothiophenol,
aminophenol, and phenylenediamine, respectively.
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Acknowledgements
CSIR-CSMCRI-Communication no. 117/2014. S.N.R. and
D.C.M. are thankful to AcSIR for Ph.D. enrollment and the
“Analytical Discipline and Centralized Instrumental Facilities”
for providing instrumentation facilities. S.N.R. and D.C.M. are
thankful to CSIR and UGC, New Delhi for their fellowship. We
thank DST, Government of India (SR/S1/OC-13/2011), for
financial support. We also thank CSIR-CSMCRI (OLP-0076) for
partial assistance.
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Notes and references
1 (a) A. Greenberg, C. M. Breneman and J. F. Liebman, The
Amide Linkage Structural Significance in Chemistry, Bio-
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