1,3-Dipolar cycloaddition reactions of 1-(3-nitrophenacyl)-1,10-phenanthrolinium N-ylide with activated alkynes

Autor:	Mihaela Cristea, Mino R. Caira, Constantin Draghici, Andrei Badoiu, Loredana Barbu, Florea Dumitrascu
Rok vydání:	2005
Předmět:	chemistry.chemical_classification Chemistry Stereochemistry Organic Chemistry Nuclear magnetic resonance spectroscopy Medicinal chemistry Cycloaddition lcsh:QD241-441 chemistry.chemical_compound lcsh:Organic chemistry Ylide 1 3-Dipolar cycloaddition Chirality (chemistry) Triethylamine
Zdroj:	Scopus-Elsevier ARKIVOC, Vol 2005, Iss 10, Pp 165-173 (2005)
ISSN:	1551-7012
DOI:	10.3998/ark.5550190.0006.a14
Popis:	The 3+2 cycloaddition reaction of 1-(3-nitrophenacyl)-1,10-phenanthrolinium ylide 4 with activated alkynes gave pyrrolo(1,2-a)(1,10)phenanthrolines 7a-e. The reaction of N-ylide 4 with DMAD, under controlled conditions, gave regioselectively the primary cycloadduct trans-5a which, in the presence of triethylamine, rearranged regio- and stereoselectively to trans-6a. Evidence for the helical chirality of pyrrolophenanthrolines 7b-e was obtained by NMR spectroscopy.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::1aa25a4d9ec438856e2ec3ce12dc34d7 https://doi.org/10.3998/ark.5550190.0006.a14 Zobrazit plný text záznamu