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2-[(1E,3E)-4-Arylbuta-1,3-dien-1-yl]-4H-chromen-4-ones as Dienes in Diels-Alder Reactions - Experimental and Computational Studies

Title
2-[(1E,3E)-4-Arylbuta-1,3-dien-1-yl]-4H-chromen-4-ones as Dienes in Diels-Alder Reactions - Experimental and Computational Studies
Type
Article in International Scientific Journal
Year
2017
Authors
Albuquerque, HMT
(Author)
Other
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Santos, CMM
(Author)
Other
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Cavaleiro, JAS
(Author)
Other
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Silva, AMS
(Author)
Other
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Journal
Vol. 2017
Pages: 87-101
ISSN: 1434-193X
Publisher: Wiley-Blackwell
Other information
Authenticus ID: P-00M-G73
Abstract (EN): The synthesis and reactivity of 2-[(1E,3E)-4-arylbuta1,3-dien-1-yl]-4H-chromen-4-ones as dienes in Diels-Alder (DA) reactions with several electron-poor and electron-rich dienophiles under microwave irradiation was studied. The optimized reaction conditions were achieved with N-methylmaleimide as the dienophile and Sc(OTf)3 (OTf = triflate) as a Lewis acid under microwave-assisted and solvent-free conditions. The Lewis acid improved the reaction yields as it prevented the adducts obtained from undergoing a second DA reaction; thus, the for-mation of a bisadduct was avoided. The alpha,beta,gamma,delta-diene of the starting chromones was the most reactive, and the computational results confirmed the experimental findings. Theoretical calculations also provided a rationale for the unexpected lack of reactivity shown by some dienophiles. The adducts prepared were dehydrogenated with 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (DDQ); however, the aza adducts were sensitive to the highly energetic reaction conditions necessary for the aromatization.
Language: English
Type (Professor's evaluation): Scientific
No. of pages: 15
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