Synthesis of functionalized 2H-1-benzopyrans by DBU-catalyzed reactions of salicylic aldehydes with allenic ketones and esters.
[reaction: see text] DBU-catalyzed reactions of salicylic aldehydes with 3-methylpenta-3,4-dien-2-one, 3-benzylpenta-3,4-dien-2-one, or ethyl 2-methylbuta-2,3-dienoate gave the corresponding functionalized 2H-1-chromenes in good to excellent yields and good diastereoselectivities in some cases in DMSO, respectively.
Zhao
Gui-Ling
GL
State Key Laboratory of Organometallic Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 354 Fenglin Lu, Shanghai 200032, China.
Shi
Yong-Ling
YL
Shi
Min
M
D000447:Aldehydes / Q000737:chemistry*; D001578:Benzopyrans / Q000138:chemical synthesis / Q000737:chemistry*; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000737:chemistry*; D002384:Catalysis; D018360:Crystallography, X-Ray; D004952:Esters / Q000737:chemistry*; D007659:Ketones / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure
D000447:Aldehydes; D001578:Benzopyrans; D019086:Bridged Bicyclo Compounds, Heterocyclic; D004952:Esters; D007659:Ketones; C031033:1,8-diazabicyclo(5.4.0)undec-7-ene