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J Org Chem. 2018 Nov 2;83(21):13308-13324. doi: 10.1021/acs.joc.8b02112. Epub 2018 Oct 24.

Metal-Free [2 + 2 + 2] Cycloaddition of Ynamide-Nitriles with Ynamides: A Highly Regio- and Chemoselective Synthesis of δ-Carboline Derivatives.

Author information

1
Key Laboratory of Marine Drugs, Chinese Ministry of Education, School of Medicine and Pharmacy , Ocean University of China , Yushan Road , Qingdao , 266003 , People's Republic of China.
2
College of Chemistry and Pharmaceutical Sciences , Qingdao Agricultural University , Qingdao 266109 , People's Republic of China.
3
Laboratory for Marine Drugs and Bioproducts Qingdao National Laboratory for Marine Science and Technology , Qingdao 266237 , People's Republic of China.

Abstract

A metal-free formal [2 + 2 + 2] cycloaddition of functionalized ynamide-nitriles with ynamides is disclosed which offers highly efficient access to polysubstituted δ-carboline derivatives under the mediation of TfOH. This strategy is highly regioselective and chemoselective and displays mild conditions, high yields, and efficiency (within 1 min) in addition to substrates scopes (56 examples).

PMID:
30353730
DOI:
10.1021/acs.joc.8b02112

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