Leimgruber–Batcho indole synthesis
The Leimgruber–Batcho indole synthesis is a series of organic reactions that produce indoles from o-nitrotoluenes 1.[1][2][3] The first step is the formation of an enamine 2 using N,N-dimethylformamide dimethyl acetal and pyrrolidine.[4] The desired indole 3 is then formed in a second step by reductive cyclisation.
In the above scheme, the reductive cyclisation is effected by
Reaction mechanism
In the initial enamine formation,
The reaction is a good example of a reaction that was widely used in industry before any procedures were published in the mainstream scientific literature. Many indoles are
The intermediate enamines are electronically related to
Variations
Dinitrostyrene reductive cyclization
The reductive cyclization of dinitrostyrenes (2) has proven itself effective when other more common methods have failed.[7]
Most of the standard reduction methods listed above are successful with this reaction.
See also
References
- ^ Batcho, A. D.; Leimgruber, W. U.S. patent 3,732,245 & U.S. patent 3,976,639
- ^ Batcho, A. D.; Leimgruber, W. Organic Syntheses 1985, 63, 214–220. (Article)
- ^ Clark, R. D.; Repke, D. B. Heterocycles 1984, 22, 195–221. (Review)
- )
- ^ Garcia, E. E.; Fryer, R. I. J. Heterocycl. Chem. 1974, 11, 219.
- )
- ^ Chen, B.-C.; Hynes, Jr., J.; Randit, C. R.; Zhao, R.; Skoumbourdis, A. P.; Wu, H.; Sundeen, J. E.; Leftheris, K. Heterocycles 2001, 55, 951-960.