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ChemInform Abstract: Copper-Catalyzed Tandem Synthesis of Indolo-, Pyrrolo[2,1-a]isoquinolines, Naphthyridines and Bisindolo/Pyrrolo[2,1-a]isoquinolines via Hydroamination of ortho-Haloarylalkynes Followed by C-2 Arylation

Authors :
Ritu Chaudhary
Abhinandan K. Danodia
Rakesh Tiwari
Akhilesh K. Verma
Kotla Siva K. Reddy
Rajeev R. Jha
Source :
ChemInform. 44
Publication Year :
2013
Publisher :
Wiley, 2013.

Abstract

An efficient approach for the copper-catalyzed regioselective tandem synthesis of diversely substituted indolo[2,1-a]isoquinolines 11a–r, pyrrolo[2,1-a]isoquinolines 12a–d, and indolo-, pyrrolo[2,1-f][1,6]naphthyridines 14a–f via preferential addition of the heterocyclic amines onto the ortho-haloarylalkynes over N-arylation followed by intramolecular C-2 arylation is described. The scope of the developed chemistry was successfully extended for the direct synthesis of bisindolo-, pyrrolo[2,1-a]isoquinolines 15a–g, a regioisomer of the bisindolo[1,2-a]quinolines used as organic single-crystal field-effect transistor. Hydroxymethyl benzotriazole, which is an inexpensive and air stable compound, has been used as a ligand to carry out this one-step conversion of simple, readily available starting materials into an interesting class of heterocyclic compounds.

Details

ISSN :
09317597
Volume :
44
Database :
OpenAIRE
Journal :
ChemInform
Accession number :
edsair.doi...........334728805fe2ac840f08220ebabd94f7
Full Text :
https://doi.org/10.1002/chin.201304108