2-(2Indenyl)indole → 6-Oxo carbazole

HRID 2392696

Reaction equation

HRID 2392696 reaction equation
C1[C:9]2[C:4](=CC=CC=2)[CH:3]=[C:2]1[C:10]1[NH:11][C:12]2[C:17]([CH:18]=1)=[CH:16][CH:15]=[CH:14][CH:13]=2.C(/C=C\C(OCC)=[O:24])#N>Cl[Sn](Cl)(Cl)Cl.[Al+3].[Cl-].[Cl-].[Cl-].C([Al](Cl)Cl)C.[Al](Cl)(CC)CC.C(O)(C(F)(F)F)=O.ClCl.C1(C)C=CC=CC=1>[O:24]=[C:4]1[CH:3]=[CH:2][C:10]2[C:18]([C:17]3[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=3[N:11]=2)=[CH:9]1

Participants

10

Reactant 2

HCID 105856192-(2Indenyl)indoleHCID 15577688Ethyl (2Z)-3-cyanoprop-2-enoate

Product 1

HCID 189804036-Oxo carbazole

Reagents, catalysts & solvents 7

HCID 1140TolueneSolventHCID 6422Trifluoroacetic acidSolventHCID 7277Diethylaluminum chlorideSolventHCID 11237Ethylaluminum dichlorideSolventHCID 24287Tin tetrachlorideSolventHCID 24526ChlorineSolventHCID 6451240Aluminum(III) ChlorideSolvent

Procedure

In Method B (FIG. 2), a 2-(heteroaryl)indole derivative (1-3), or 2-(aryl)indole derivative such as 2-(2indenyl)indole 4 is reacted with ethyl cis-β-cyanoacrylate in the presence of a catalyst such as SnCl4, AlCl3, EtAlCl2, Et2AlCl or TFA in CH2 Cl2, C2H4Cl2 or toluene as solvent to give the 6-oxo carbazole compounds of formula I of the invention.

Sources & evidence

ORD record
ord-91e8c78440314a209782ee3b072a0f3c
Source dataset
uspto-grants-1998_09
Patent number
US05801190

Linked notes

Loading…