Utilize este identificador para referenciar este registo: http://hdl.handle.net/10198/15347
Título: 1,6-Conjugate Additions of Carbon Nucleophiles to 2-[(1E,3E)-4-Arylbuta-1,3-dien-1-yl]-4H-chromen-4-ones
Autor: Albuquerque, Hélio
Santos, Clementina M.M.
Balanay, Mannix P.
Cavaleiro, José
Silva, Artur
Palavras-chave: Conjugate addition
Density functional calculations
Nitrogen heterocycles
Oxygen heterocycles
Data: 2017
Citação: Albuquerque, Hélio M.T.; Santos, Clementina M.M.; Balanay, Mannix P.; Cavaleiro, José A.S.; Silva, Artur M.S. (2017). 1,6-Conjugate Additions of Carbon Nucleophiles to 2-[(1E,3E)-4-Arylbuta-1,3-dien-1-yl]-4H-chromen-4-ones. European Journal of Organic Chemistry. ISSN 1434-193X. 2017, p. 5293-5305
Resumo: KGaA, Weinheim The 1,6-conjugate addition of nitromethane to 2-[(1E,3E)-4-arylbuta-1,3-dien-1-yl]-4H-chromen-4-ones was accomplished and led mainly to the corresponding β-(nitromethyl)chromones. (E)-5′-(Nitromethyl)-3′-styryl-[1,1′-biphenyl] -2-ol and 3′-aryl-2′-nitro-5′-(nitromethyl)spiro[chromane-2,1′-cyclohexan]-4-one derivatives were also isolated as minor products from tandem processes, which result from the addition of a second molecule of nitromethane. The nucleophile scope was investigated with malononitrile, acetylacetone, ethyl cyanoacetate, and diethyl malonate, which gave the expected 1,6-addition products; in the last case, it was also possible to isolate a minor product formed through a 1,8-/1,6-addition sequence. Computational calculations provided a rationale for the experimental reactivity of carbon nucleophiles with 2-[(1E,3E)-4-arylbuta-1,3-dien-1-yl] -4H-chromen-4-ones. The further functionalization of some adducts allowed the preparation of new nitrogen-containing heterocyclic compounds, such as new styrylpyrrolidines and new pyrazole and bis(pyrazole) derivatives.
Peer review: yes
URI: http://hdl.handle.net/10198/15347
DOI: 10.1002/ejoc.201700944
ISSN: 1434-193X
Aparece nas colecções:CIMO - Artigos em Revistas Indexados à WoS/Scopus

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