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

Research output: Contribution to journalArticle

4 Citations (Scopus)

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 languageEnglish (US)
Pages (from-to)5429-5433
Number of pages5
JournalTetrahedron Letters
Volume56
Issue number40
DOIs
StatePublished - Sep 30 2015

Fingerprint

Phenylcarbamates
Isoquinolines
Cyclization
Alkylation
Bromides
Amines
Transition metals
Photoluminescence
Metals
Atoms
Substrates

Keywords

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

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Drug Discovery

Cite this

Expedient one-pot synthesis of indolo[3,2-c]isoquinolines via a base-promoted N-Alkylation/tandem cyclization. / Nguyen, Huy H.; Fettinger, James C.; Haddadin, Makhluf J.; Kurth, Mark J.

In: Tetrahedron Letters, Vol. 56, No. 40, 30.09.2015, p. 5429-5433.

Research output: Contribution to journalArticle

Nguyen, Huy H. ; Fettinger, James C. ; Haddadin, Makhluf J. ; Kurth, Mark J. / Expedient one-pot synthesis of indolo[3,2-c]isoquinolines via a base-promoted N-Alkylation/tandem cyclization. In: Tetrahedron Letters. 2015 ; Vol. 56, No. 40. pp. 5429-5433.
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