Expedient one-pot synthesis of indolo[3,2-c]isoquinolines via a base-promoted N-Alkylation/tandem cyclization

Huy H. Nguyen; James C. Fettinger; Makhluf J. Haddadin; Mark J. Kurth

doi:10.1016/j.tetlet.2015.08.006

Expedient one-pot synthesis of indolo[3,2-c]isoquinolines via a base-promoted N-Alkylation/tandem cyclization

Huy H. Nguyen, James C. Fettinger, Makhluf J. Haddadin, Mark J. Kurth

Chemistry

Research output: Contribution to journal › Article

4 Scopus citations

Abstract

A transition metal-free, one-pot protocol has been developed for the synthesis of 11H-indolo[3,2-c]isoquinolin-5-amines via the atom economical annulation of ethyl (2-cyano-phenyl)carbamates and 2-cyanobenzyl bromides. This method proceeds via sequential N-alkylation and base-promoted cyclization. Optimization data, substrate scope, mechanistic insights, and photoluminescence properties are discussed.

Original language	English (US)
Pages (from-to)	5429-5433
Number of pages	5
Journal	Tetrahedron Letters
Volume	56
Issue number	40
DOIs	https://doi.org/10.1016/j.tetlet.2015.08.006
State	Published - Sep 30 2015

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Keywords

Domino process
Indolo[3,2-c]isoquinoline
One-pot
Photoluminescence
Tandem cyclization

ASJC Scopus subject areas

Biochemistry
Organic Chemistry
Drug Discovery

Cite this

Nguyen, H. H., Fettinger, J. C., Haddadin, M. J., & Kurth, M. J. (2015). Expedient one-pot synthesis of indolo[3,2-c]isoquinolines via a base-promoted N-Alkylation/tandem cyclization. Tetrahedron Letters, 56(40), 5429-5433. https://doi.org/10.1016/j.tetlet.2015.08.006

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AU - Haddadin, Makhluf J.

AU - Kurth, Mark J.

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KW - Photoluminescence

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10.1016/j.tetlet.2015.08.006