Tandem Synthesis of Pyrroloacridones via [3 + 2] Alkyne Annulation/Ring-Opening with Concomitant Intramolecular Aldol Condensation

Autor:	Akhilesh K. Verma, Siva K. Reddy Kotla, Rakesh Tiwari, Sonu Kumar, Hemlata Nimesh, Trapti Aggarwal
Rok vydání:	2013
Předmět:	chemistry.chemical_classification Aldehydes Annulation Molecular Structure Tandem Stereochemistry Organic Chemistry Condensation Alkyne Regioselectivity Ring (chemistry) Combinatorial chemistry chemistry Cyclization Alkynes Intramolecular force Acridines Pyrroles Aldol condensation Microwaves
Zdroj:	The Journal of Organic Chemistry. 78:5372-5384
ISSN:	1520-6904 0022-3263
DOI:	10.1021/jo400539x
Popis:	An efficient cascade strategy for the direct synthesis of pyrrolo[3,2,1-de]acridones 4a-v, 5a-h from iodo-pyranoquinolines 2a-i by the palladium-catalyzed regioselective [3 + 2] alkyne annulation/ring-opening followed by intramolecular aldol condensation under microwave irradiation is described. The chemistry involves the in situ formation of pyrroloquinolines Y, via palladium-catalyzed selective [3 + 2] annulation of iodopyranoquinolines and internal akynes with ring-opening and successive intramolecular cross-aldol condensation. Both the symmetrical and unsymmetrical internal alkynes were reacted smoothly to provide the desired pyrroloacridones in good yields. This methodology provides the facile conversion of easily accessble iodopyranoquinoline into highly functionalized biologically important pyrroloacridones in a single process.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::7a241fb2ab4bf1ad7fca8ea5472ea189 https://doi.org/10.1021/jo400539x Zobrazit plný text záznamu