DABCO and Bu3P catalyzed [4 + 2] and [3 + 2] cycloadditions of 3-acyl-2H-chromen-ones and ethyl 2,3-butadienoate.
DABCO-catalyzed [4 + 2] and Bu(3)P-catalyzed [3 + 2] cycloadditions between 3-acyl-2H-chromen-ones and ethyl 2,3-butadienoate were developed for the synthesis of dihydropyran-fused and cyclopenten-fused chromen-2-ones with high regio- and stereo-selectivities, respectively. The synthetic procedures have the advantages of mild reaction conditions, convenient handling and good atom economy as well as a wide substrate scope, which make this method useful for the synthesis of potentially biologically active dihydropyran-fused and cyclopenten-fused chromen-2-ones derivatives. Possible reaction mechanisms have also been proposed on the basis of previous literature and our investigation.
Key Laboratory of Pesticide and Chemical Biology of Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079, People's Republic of China.
Ying
Y
Wang
Zhi-Hua
ZH
Yu
Hu-Fei
HF
Zheng
De-Qing
DQ
Shi
D002070:Butadienes / Q000737:chemistry*; D002384:Catalysis; D002867:Chromones / Q000138:chemical synthesis* / Q000737:chemistry; D003500:Cyclization; D015394:Molecular Structure; D010755:Organophosphates / Q000737:chemistry*; D010879:Piperazines / Q000737:chemistry*
D002070:Butadienes; D002867:Chromones; D010755:Organophosphates; D010879:Piperazines; C580779:ethyl 2,3-butadienoate; C009524:tributyl phosphate; C007306:triethylenediamine