Biomaterial Database

Acid-promoted cascade cyclization to produce fused-polycyclic indole derivatives. 2013

Takuya Yokosaka, and Hiroki Nakayama, and Tetsuhiro Nemoto, and Yasumasa Hamada

Graduate School of Pharmaceutical Sciences, Chiba University , 1-8-1, Inohana, Chuo-ku, Chiba, 260-8675, Japan.

An acid-promoted novel cascade cyclization is described. Using 8 equiv of trifluoroacetic acid or a catalytic amount of Lewis acid as the promoter, structurally diverse polycyclic cyclopenta[b]indoles were obtained in moderate to excellent yield. This cascade process was extremely effective for the synthesis of 8-membered ring-fused cyclopenta[b]indole derivatives.

UI	MeSH Term	Description	Entries
D007211	Indoles	Benzopyrroles with the nitrogen at the number one carbon adjacent to the benzyl portion, in contrast to ISOINDOLES which have the nitrogen away from the six-membered ring.
D002384	Catalysis	The facilitation of a chemical reaction by material (catalyst) that is not consumed by the reaction.	Catalyses
D003500	Cyclization	Changing an open-chain hydrocarbon to a closed ring. (McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed)	Cyclizations
D013237	Stereoisomerism	The phenomenon whereby compounds whose molecules have the same number and kind of atoms and the same atomic arrangement, but differ in their spatial relationships. (From McGraw-Hill Dictionary of Scientific and Technical Terms, 5th ed)	Molecular Stereochemistry,Stereoisomers,Stereochemistry, Molecular,Stereoisomer
D014269	Trifluoroacetic Acid	A very strong halogenated derivative of acetic acid. It is used in acid catalyzed reactions, especially those where an ester is cleaved in peptide synthesis.	Trifluoroacetate,Cesium Trifluoroacetate,Acid, Trifluoroacetic,Trifluoroacetate, Cesium
D015394	Molecular Structure	The location of the atoms, groups or ions relative to one another in a molecule, as well as the number, type and location of covalent bonds.	Structure, Molecular,Molecular Structures,Structures, Molecular
D058116	Lewis Acids	Any chemical species which accepts an electron-pair from a LEWIS BASE in a chemical bonding reaction.	Lewis Acid,Acid, Lewis,Acids, Lewis