Display options
Cite
Li B, Zhang B, Zhang X, et al. Synthesis of 3-Cyano-1H-indoles and Their 2'-Deoxyribonucleoside Derivatives through One-Pot Cascade Reactions. J Org Chem. 2016;81(20):9530-9538doi: 10.1021/acs.joc.6b01612.
Li, B., Zhang, B., Zhang, X., & Fan, X. (2016). Synthesis of 3-Cyano-1H-indoles and Their 2'-Deoxyribonucleoside Derivatives through One-Pot Cascade Reactions. The Journal of organic chemistry, 81(20), 9530-9538. https://doi.org/10.1021/acs.joc.6b01612
Li, Bin, et al. "Synthesis of 3-Cyano-1H-indoles and Their 2'-Deoxyribonucleoside Derivatives through One-Pot Cascade Reactions." The Journal of organic chemistry vol. 81,20 (2016): 9530-9538. doi: https://doi.org/10.1021/acs.joc.6b01612
Li B, Zhang B, Zhang X, Fan X. Synthesis of 3-Cyano-1H-indoles and Their 2'-Deoxyribonucleoside Derivatives through One-Pot Cascade Reactions. J Org Chem. 2016 Oct 21;81(20):9530-9538. doi: 10.1021/acs.joc.6b01612. Epub 2016 Aug 15. PMID: 27513004.
Copy Download .nbib Format: NLM
Share it on

J Org Chem. 2016 Oct 21;81(20):9530-9538. doi: 10.1021/acs.joc.6b01612. Epub 2016 Aug 15.

Synthesis of 3-Cyano-1H-indoles and Their 2'-Deoxyribonucleoside Derivatives through One-Pot Cascade Reactions.

The Journal of organic chemistry

Bin Li, Beibei Zhang, Xinying Zhang, Xuesen Fan

Affiliations

  1. Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, School of Environment, School of Chemistry and Chemical Engineering, Key Laboratory of Green Chemical Media and Reactions, Ministry of Education, Henan Normal University , Xinxiang, Henan 453007, China.

PMID: 27513004 DOI: 10.1021/acs.joc.6b01612

Abstract

An efficient and economical synthetic approach toward 3-cyano-1H-indoles through the reactions of 2-(2-bromophenyl)acetonitriles with aldehydes and aqueous ammonia is presented. Mechanically, this novel protocol involves a one-pot cascade procedure consisting of an aldol-type condensation, a copper-catalyzed amination by using aqueous ammonia as a cheap and safe nitrogen source, and an intramolecular Michael addition followed by a dehydrogenative aromatization. Interestingly, the indole products thus obtained were found to be ready substrates for the preparation of indole 2'-deoxyribonucleosides through an unprecedented and highly practical glycosylation procedure in which the required C-N bond formation and toluoyl protecting group removal were accomplished efficiently in one pot.

Publication Types