Global InformationNenitzescu indole synthesis information
| Nenitzescu indole synthesis | |
|---|---|
| Named after | Costin Nenițescu |
| Reaction type | Ring forming reaction |
The Nenitzescu indole synthesis is a chemical reaction that forms 5-hydroxyindole derivatives from benzoquinone and β-aminocrotonic esters.
This reaction was named for its discoverer, Costin Nenițescu, who first reported it in 1929.[1] It can be performed with a number of different combinations of R-groups, which include methyl, methoxy, ethyl, propyl, and H substituents.[2] There is also a solid-state variation in which the reaction takes place on a highly cross-linked polymer scaffold.[3] The synthesis is particularly interesting because indoles are the foundation for a number of biochemically important molecules, including neurotransmitters and a new class of antitumor compounds.[4]
- ^ Nenitzescu, C.D. (1929). "Derivatives of 2-methyl-5-hydroxyindole". Bull. Soc. Chim. Romania. 11: 37–43.
- ^ Allen, G.; Pidacks, C.; Weiss, M. (5 June 1996). "The Mitomycin Antibiotics. Synthetic Studies". J. Am. Chem. Soc. 88 (11): 2536–2544. doi:10.1021/ja00963a032. PMID 5941382.
- ^ Ketcha, Daniel M.; Wilson, L.J.; Portlock, D.E. (2000). "The solid-phase Nenitzescu indole synthesis". Tetrahedron Letters. 41 (33): 6253–6257. doi:10.1016/S0040-4039(00)00697-3.
- ^ Schenck, Lothar Werner; Kuna, K.; Frank, W.; Albert, A.; Asche, C.; Kucklaender, U. (10 January 2006). "1,4,9,10-Anthradiquinone as precursor for antitumor compounds". Bioorganic & Medicinal Chemistry. 14 (10): 3599–3614. doi:10.1016/j.bmc.2006.01.026. PMID 16458517.