Microwave-Promoted Synthesis ofN-Heterocycles by Tandem Imination/Annulation of γ- and δ-Ketoalkynes in the Presence of Ammonia

Autor:	Giorgio Abbiati, Maria Alfonsi, Antonio Arcadi, Diego Facoetti, Elisabetta Rossi, Monica Dell'Acqua
Rok vydání:	2009
Předmět:	Titanium chemistry.chemical_classification Reaction mechanism Annulation Ketone Organic Chemistry Domino reactions Microwaves Regioselectivity Alkyne Chemical synthesis chemistry Cascade reaction Intramolecular force Organic chemistry Physical and Theoretical Chemistry
Zdroj:	European Journal of Organic Chemistry. 2009:2852-2862
ISSN:	1099-0690 1434-193X
DOI:	10.1002/ejoc.200900014
Popis:	The synthesis of 3-substituted 1-methylpyrrolo[1,2-a]pyrazines and 3-substituted isoquinolines was achieved by the intramolecular cyclisation of 2-acetyl-1-propargylpyrroles and 2-alkynylbenzaldehydes, respectively, in the presence of ammonia under microwave heating. The tandem imination/annulation of 2-alkynylbenzaldehydes was easily accomplished under standard conditions, while TiCl4 was used to achieve pyrrolo[1,2-a]pyrazines. The reaction mechanism and the regioselectivity were discussed on the basis of theoretical calculations and spectroscopic data. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_dedup___::2789556e227da9648a42e5bbd2c67ec3 https://doi.org/10.1002/ejoc.200900014 Zobrazit plný text záznamu Plný text