Stereoselective Synthesis ofcis-2 andtrans-2-(Indol-3-yl) Cyclopropyl Amines, Carboxylic Acids, and Esters

Autor:	Maurice R. Eftink, Tilak T. Raj
Rok vydání:	1998
Předmět:	Indole test Tryptamine chemistry.chemical_compound Hydrolysis Ethyl diazoacetate Chemistry Organic Chemistry Organic chemistry Stereoselectivity E-Z notation Curtius rearrangement Cyclopropane
Zdroj:	Synthetic Communications. 28:3787-3794
ISSN:	1532-2432 0039-7911
DOI:	10.1080/00397919808004931
Popis:	We report a general route for the synthesis of E and Z isomers of indol-3-yl cyclopropyl amines, carboylic acids, and esters. These cyclopropane containing molecules are of interest as conformationally constrained analogues of tryptamine and indole propionic acid, biologically active indoles. The route involves reaction of vinyl indole with ethyl diazoacetate, chromatographic separation of the E and Z stereoisomers of the resulting cyclopropane esters, hydrolysis to form the E and Z cyclopropane acids, and formation of amines by the Curtius reaction.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::4a7d24bb4e8cbcc2b887dab046497a85 https://doi.org/10.1080/00397919808004931 Zobrazit plný text záznamu