Pt(IV)-catalyzed hydroamination triggered cyclization: a strategy to fused pyrrolo[1,2-a]quinoxalines, indolo[1,2-a]quinoxalines, and indolo[3,2-c]quinolines.
A PtCl(4)-catalyzed hydroamination-triggered cyclization strategy to access biologically interesting N-containing heterocycles such as pyrrolo[1,2-a]quinoxalines, indolo[1,2-a]quinoxalines, and indolo[3,2-c]quinolines is described. The reaction makes use of aminoaromatics such as 1-(2-aminophenyl)pyrroles, N-(2-aminophenyl)indoles, 2-(2-aminophenyl)indoles, and alkynes having a tethered hydroxyl group. Mechanistically, the reaction is very appealing since it involves multiple catalytic cycles catalyzed by a single metal catalyst PtCl(4). We observed a remarkable enhancement of the rate when reactions were run under microwave-assisted conditions.
Patil
Nitin T
NT
Organic Chemistry Division II, Indian Institute of ChemicalTechnology, Hyderabad 500 607, India. nitin@iict.res.in
Kavthe
Rahul D
RD
Shinde
Valmik S
VS
Sridhar
Balasubramanian
B
D000586:Amination; D002384:Catalysis; D003500:Cyclization; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D007211:Indoles / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D010984:Platinum / Q000737:chemistry*; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry; D011804:Quinolines / Q000138:chemical synthesis* / Q000737:chemistry; D011810:Quinoxalines / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D006571:Heterocyclic Compounds; D007211:Indoles; D011758:Pyrroles; D011804:Quinolines; D011810:Quinoxalines; C531444:pyrrolo(1,2-a)quinoxaline; D010984:Platinum