69490-59-1Relevant academic research and scientific papers
Ready Access to Densely Substituted Furans Using Tsuji-Wacker-Type Cyclization
Masal, Dattatraya P.,Choudhury, Rahul,Singh, Aman,Reddy, D. Srinivasa
, p. 556 - 568 (2022/01/14)
A competent method for the construction of highly substituted furans catalyzed by Pd(II) and Cu(II) chloride has been developed. The method provides easy access to di-, tri-, and tetrasubstituted furans from corresponding diols with relatively mild condit
Copper-catalyzed, silver-mediated formal [3+2] cycloaddition of simple alkynes with β-ketoesters through propargylic C(sp3)-H functionalization
Liu, Zhen-Ting,Hu, Xiang-Ping
, p. 14100 - 14103 (2019/01/03)
A copper-catalyzed propargylic [3+2] cycloaddition of simple alkynes with β-ketoesters through the propargylic C(sp3)-H functionalization has been realized. Under catalysis by CuI in combination with 1,10-phenanthroline hydrate as the ligand and Ag2CO3 as a bifunctional reagent (oxidant and base), the reaction proceeds smoothly with a broad substrate scope, thus providing a variety of highly functionalized furans in moderate to high yields. This represents the first successful example of the catalytic propargylic cycloaddition of simple alkynes with bisnucleophiles based on the propargylic C(sp3)-H functionalization strategy.
Triplet photochemistry of acyl and imino cyclopropenes. a rearrangement to afford furans and pyrroles: Reaction and mechanism
Zimmerman, Howard E.,Wright, Charles W.
, p. 6603 - 6612 (2007/10/02)
Syntheses of 3-substituted 3-acylcyclopropenes and 3-benzoylcyclopropene imines were devised. A triplet rearrangement of acylcyclopropenes having C-3 aryl substitution to afford furans has been uncovered and studied with several examples. Unlike the singl
SYNTHESIS OF FURANS BY ACYLATION OF CYCLOPROPENES
Bartmann, Ekkehard,Gompper, Rudolf
, p. 263 - 270 (2007/10/02)
Cyclopropenes substituted with phenyl groups at the double bond react with acyl chlorides in the presence of aluminium chloride under formation of phenyl substituted furans.
Photochemistry of Cyclopropene Derivatives. Synthesis and Photorearrangement of a 3-Acyl-Substituted Cyclopropene
Padwa, Albert,Akiba, Mitsuo,Chou, Chuen S.,Cohen, Leslie
, p. 183 - 191 (2007/10/02)
Two different approaches toward the synthesis of a 3-acyl-substituted 1,2,3-triphenylcyclopropene were investigated.The first involved treating triphenylcyclopropenyl perchlorate with the anion derived from 1,3-dithiane followed by hydrolysis of the resulting dithioacetal.Unfortunately, all attempts to obtain a carbonyl compound from the hydrolysis failed.The only product obtained corresponded to a 1,2-diphenyl-1,2-diacyl-substituted alkene.The second approach utilized for the synthesis involved treating 3-cyano-1,2,3-triphenylcyclopropene with methyllithium.The addition proceeded quite smoothly to give the desired 3-acetyl derivative in high yield.Irradiation of 1,2,3-triphenyl-3-acetylcyclopropene in benzene afforded a mixture of 2,3,4-triphenyl-2-cyclopentenone (60percent), 2-methyl-3,4,5-triphenylfuran (27percent), and 3-acetyl-1,2-diphenylindene (13percent).The formation of the three products obtained can be rationalized in terms of a vinylcarbene intermediate.Several different pathways are available to this species, depending on the stereochemistry about the double bond and on the conformation the oxygen atom assumes in the cis intermediate.The formation of the 2-cyclopentenone derivative provides good support for the mechanism proposed some years ago to rationalize the photochemical rearrangement of 2,5-dimethylfuran.
