A Novel Fragmentation of 7-Azabicyclo[2.2.1]hepta-2,5-dienes: Synthesis ofcis-5-Amidino-pyrrolidine-2-acetic Acid Derivatives

Autor:	Christoph Hoenke, Peter Bäuerle, Volkhard Austel, Dirk Weber, Eberhard Heller, Stefan Hörer
Rok vydání:	2005
Předmět:	chemistry.chemical_compound Acetic acid chemistry Fragmentation (mass spectrometry) Nucleophile Organic Chemistry Enantioselective synthesis Organic chemistry Pyrroline Ring (chemistry) Cleavage (embryo) Catalysis Pyrrolidine
Zdroj:	Synthesis. :2357-2366
ISSN:	1437-210X 0039-7881
DOI:	10.1055/s-2005-870011
Popis:	A new fragmentation reaction of 3-bromo-7-azabicy-clo[2.2.1]hepta-2,5-diene carboxylic esters with 2-amino or 2-aminomethyl anilines is described. It leads to cis-5-(benzimidazol-2-yl)- or cis-5-(3,4-dihydroquinazolin-2-yl)-pyrroline-2-acetic acid esters. Substituents on the nitrogen atoms or in the aromatic ring are tolerated as long as they do not strongly reduce the nucleophilicity of the nitrogen atoms. The primary reaction products are not very stable but hydrogenation of the pyrroline and/or cleavage of the ester give products that are suitable for subsequent structural modifications, particularly ones that are interesting for combinatorial syntheses.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::183f7dbd1de02f2e61a14b8ced573f44 https://doi.org/10.1055/s-2005-870011