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A Facile Synthetic Route to 2 H ‐Chromenes: Reconsideration of the Mechanism of the DBU‐Catalyzed Reaction between Salicylic Aldehydes and Ethyl 2‐Methylbuta‐2,3‐dienoate
Author(s) -
Dai LunZhi,
Shi YongLing,
Zhao GuiLing,
Shi Min
Publication year - 2007
Publication title -
chemistry – a european journal
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 1.687
H-Index - 242
eISSN - 1521-3765
pISSN - 0947-6539
DOI - 10.1002/chem.200601033
Subject(s) - catalysis , chemistry , reaction mechanism , potassium carbonate , mechanism (biology) , combinatorial chemistry , organic chemistry , philosophy , epistemology
Reactions of salicylaldehydes with ethyl buta‐2,3‐dienoate or penta‐3,4‐dien‐2‐one catalyzed by a catalytic amount of potassium carbonate produce the corresponding 2 H ‐chromene products in moderate to good yields under mild conditions. A plausible reaction mechanism is discussed in the light of the results of an 18 O‐labeling experiment. In addition, in view of these findings, the catalytic function of DBU in reactions of this kind is reconsidered.