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 › peer-review

6 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

Keywords

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

ASJC Scopus subject areas

Biochemistry
Organic Chemistry
Drug Discovery

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

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.",

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

author = "Nguyen, {Huy H.} and Fettinger, {James C.} and Haddadin, {Makhluf J.} and Kurth, {Mark J.}",

year = "2015",

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pages = "5429--5433",

journal = "Tetrahedron Letters",

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T1 - Expedient one-pot synthesis of indolo[3,2-c]isoquinolines via a base-promoted N-Alkylation/tandem cyclization

AU - Nguyen, Huy H.

AU - Fettinger, James C.

AU - Haddadin, Makhluf J.

AU - Kurth, Mark J.

PY - 2015/9/30

Y1 - 2015/9/30

N2 - 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.

AB - 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.

KW - Domino process

KW - Indolo[3,2-c]isoquinoline

KW - One-pot

KW - Photoluminescence

KW - Tandem cyclization

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JO - Tetrahedron Letters

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