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Synthesis of 1H,7H,12bH-Pyrano[3′,4′: 5,6]pyrano[3,4-c][1]benzopyran-1-one via Domino Knoevenagel/Hetero-DielsAlder Reaction with Theoretical Investigations

✍ Scribed by Malihe Javan Khoshkholgh; Mohammad Reza Hosseindokht; Saeed Balalaie; Mohammad Reza Bozorgmehr; Hamid Reza Bijanzadeh

Publisher
John Wiley and Sons
Year
2012
Tongue
German
Weight
237 KB
Volume
95
Category
Article
ISSN
0018-019X

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✦ Synopsis

Dedicated to Prof. Lutz F. Tietze on the occasion of his 70th birthday

The CuI-catalyzed intramolecular oxa-DielsÀAlder reaction of 2-(prop-2-yn-1-yloxy)benzaldehydes as unactivated terminal alkynes with 4-hydroxy-6-methyl-2H-pyran-2-one is described. The reaction proceeds with remarkable chemoselectivity to yield pyranones 3 (Scheme 1). A theoretical investigation of the reaction in terms of HOMOÀLUMO interactions in the gas phase is also reported. The reaction could be regarded as an inverse-electron-demand DielsÀAlder cycloaddition. The theoretical results are in high agreement with the experimental evidences. 35 Cl 2 O þ 4 ; calc. 335.9956), 337.9945 ([M þ 2] þ , C 16 H 10 37 Cl 35 ClO þ 4 ; calc. 337.9927), 339.9952 ([M þ 4] þ , C 16 H 10 37 Cl 2 O þ 4 ; calc. 339.9897).

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