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Rasheed S, Rao DN, Das P. Copper-Catalyzed Inter- and Intramolecular C-N Bond Formation: Synthesis of Benzimidazole-Fused Heterocycles. J Org Chem. 2015;80(18):9321-7doi: 10.1021/acs.joc.5b01396.
Rasheed, S., Rao, D. N., & Das, P. (2015). Copper-Catalyzed Inter- and Intramolecular C-N Bond Formation: Synthesis of Benzimidazole-Fused Heterocycles. The Journal of organic chemistry, 80(18), 9321-7. https://doi.org/10.1021/acs.joc.5b01396
Rasheed, Sk, et al. "Copper-Catalyzed Inter- and Intramolecular C-N Bond Formation: Synthesis of Benzimidazole-Fused Heterocycles." The Journal of organic chemistry vol. 80,18 (2015): 9321-7. doi: https://doi.org/10.1021/acs.joc.5b01396
Rasheed S, Rao DN, Das P. Copper-Catalyzed Inter- and Intramolecular C-N Bond Formation: Synthesis of Benzimidazole-Fused Heterocycles. J Org Chem. 2015 Sep 18;80(18):9321-7. doi: 10.1021/acs.joc.5b01396. Epub 2015 Sep 08. PMID: 26322501.
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J Org Chem. 2015 Sep 18;80(18):9321-7. doi: 10.1021/acs.joc.5b01396. Epub 2015 Sep 08.

Copper-Catalyzed Inter- and Intramolecular C-N Bond Formation: Synthesis of Benzimidazole-Fused Heterocycles.

The Journal of organic chemistry

Sk Rasheed, D Nageswar Rao, Parthasarathi Das

Affiliations

  1. Jammu Campus, Academy of Scientific and Innovative Research (AcSIR) , Jammu 180001, India.
  2. Medicinal Chemistry Division, Indian Institute of Integrative Medicine(CSIR) , Jammu 180001, India.

PMID: 26322501 DOI: 10.1021/acs.joc.5b01396

Abstract

A Cu (II)-catalyzed, inter/intramolecular C-N bond formation for the synthesis of various benzimidazole-fused heterocycles in a concise manner has been reported. The robustness of this reaction is demonstrated by the synthesis of a series of benzimidazole-fused heteroaromatics (e.g., pyrido[1,2-a] benzimidazole, benzimidazo[1,2-a]quinolines, benzimidazo [1,2-a]pyrazine, benzo[4,5] imidazo[2,1-b]thiazoles) directly from 2-aminoheteroarenens and 2-iodoarylboronic acids in one-pot. The novel cascade protocol for C-N bond formation operates via unique combination of Chan-Lam type coupling followed by Ullmann-type reaction.

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