Journal
JOURNAL OF ORGANIC CHEMISTRY
Volume 81, Issue 20, Pages 9530-9538Publisher
AMER CHEMICAL SOC
DOI: 10.1021/acs.joc.6b01612
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Funding
- National Natural Science Foundation of China (NSFC) [21272058, 21572047]
- Program for Innovative Research Team in Science and Technology in Universities of Henan Province [15IRTSTHN003]
- Program for Science and Technology Innovation Talents in Universities of Henan Province [15HASTIT005]
- PCSIRT [IRT 1061]
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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.
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