4.7 Article

N,N-Dimethylacetamide (DMA) as a Methylene Synthon for Regioselective Linkage of Imidazo[1,2-a]pyridine

Journal

ADVANCED SYNTHESIS & CATALYSIS
Volume 358, Issue 13, Pages 2100-2107

Publisher

WILEY-V C H VERLAG GMBH
DOI: 10.1002/adsc.201600067

Keywords

CH activation; copper catalysis; cross dehyrogenative coupling; N; N-dimethylacetamide (DMA); DMA as methylene source; imidazo[1; 2-a]pyridines

Funding

  1. Department of Science and Technology (DST), New Delhi [(SB/S1/OC-53/2013) MHRD: 5-5/2014-TS-VII]
  2. Council of Scientific and Industrial Research (CSIR) [02(0096)/12/EMR-II]
  3. CSIR, New Delhi

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A copper(II)-catalyzed oxidative methylene-bridged dimerization of two analogous imidazo[1,2-a]pyridines has been achieved using N,N-dimethylacetamide (DMA) as solvent cum methylene source. This reaction works with a variety of substituted imidazo[1,2-a]pyridines giving their products in moderate to good yields. Isotopic labelling experiments revealed that the methylene group in the product originates from the N,N-dimethyl moiety of DMA.

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