Copper-Catalyzed Three-Component Synthesis of Polysubstituted Pyrroles

Content Provider	Scilit
Copyright Year	2011
Description	A synthesis of polysubstituted pyrroles is described. Starting from α-diazoketones, nitroalkenes, and amines, the three-component reaction proceeds under mild conditions to afford diverse tri- and tetrasubstituted 2-benzoyl pyrroles in moderate yields. A mechanism is suggested involving an NH insertion of carbene, a copper-catalyzed oxidative dehydrogenation of amine, and a [3+2] cycloaddition of azomethine ylide to an intermediate pyrrolidine (as evidence, pyrrolidine A was isolated and confirmed by X-ray crystal structure analysis), followed by thermal extrusion of $HNO_{2}$ and dehydrogenative aromatization to the pyrrole. However, this process failed for amines bearing alkyl and secondary amine groups in $R^{4}$ position.
Related Links	http://www.thieme-connect.de/products/ejournals/pdf/10.1055/s-0031-1289279.pdf
Ending Page	1172
Page Count	1
Starting Page	1172
ISSN	18611958
e-ISSN	1861194X
DOI	10.1055/s-0031-1289279
Journal	Synfacts
Issue Number	11
Volume Number	2011
Language	English
Publisher	Georg Thieme Verlag KG
Publisher Date	2011-10-19
Access Restriction	Open
Subject Keyword	Journal: Synfacts Organic Chemistry
Content Type	Text
Resource Type	Article