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.
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.
Synthetic Organic Chemistry Research Laboratory, Department of Chemistry, University of Delhi, Delhi, 110007, India. averma@acbr.du.ac.in
Akhilesh K
AK
Verma
Rajeev R
RR
Jha
Ritu
R
Chaudhary
Rakesh K
RK
Tiwari
Kotla Siva K
KS
Reddy
Abhinandan
A
Danodia
D000586:Amination; D002384:Catalysis; D003300:Copper / Q000737:chemistry*; D006846:Hydrocarbons, Halogenated / Q000737:chemistry*; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry*; D007546:Isoquinolines / Q000138:chemical synthesis* / Q000737:chemistry*; D015394:Molecular Structure; D009287:Naphthyridines / Q000138:chemical synthesis* / Q000737:chemistry*; D013237:Stereoisomerism
D006846:Hydrocarbons, Halogenated; D007211:Indoles; D007546:Isoquinolines; D009287:Naphthyridines; D003300:Copper