110595-68-1Relevant academic research and scientific papers
REACTIONS OF UNASATURATED COMPOUNDS. CL. REGIOCHEMISTRY AND STEREOCHEMISTRY OF THE ACYLATION OF 2-METHYL-1-BUTEN-3-YNE. THE TRANSFORMATION OF 2H-PYRAN INTO FURAN WITH OXIDATIVE EXTRUSION OF THE CH2 GROUP
Melikyan, G. G.,Babayan, E. V.,Panosyan, G. A.,Palikyan, G. U.,Badanyan, Sh. O.
, p. 830 - 836 (2007/10/02)
The regiochemistry and stereochemistry of the low-temperature acylation of 2-methyl-1-buten-3-yne were investigated.In the case of alkanoyl chlorides 1,4-addition of the acylating agent occurs and is followed by 1,3-chlorotropy in the adducts (1-chloro-2-
53. Acid-Catalyzed Cyclization Rections of Substituted Acetylenic Ketones: A New Approach for the Synthesis of 3-Halofurans, Flavones, and Styrylchromones
Obrecht, Daniel
, p. 447 - 456 (2007/10/02)
Acetylenic acetals of type I (Scheme 1) and acetylenic ketones of type III (Scheme 1), 37 and 38 (Scheme 7) are versatile synthetic precursors for the synthesis of various heterocycles by acid-catalyzed cyclization reactions.By this way, substituted 3-halofurans of type II and IV (Scheme 1) and flavones and styrylchromones (Scheme 7) can be synthesized in good-to-excellent yields.The high degree of regioselectivity in the synthesis of the 3-halofurans (Scheme 4) is the result of the regioselective β-addition of HX (X = Cl, Br, I) to the acetylenic aldehyde and acetylenic ketone moieties.A possible mechanism is depicted in Scheme 5.Since 3-halofurans can easily be metalated and substituted, this approach constitutes a new synthesis of highly substituted furans.
