5369-56-2Relevant academic research and scientific papers
Reactions of alkyl 4-hydroxybut-2-ynoates with arenes under superelectrophilic activation with triflic acid or HUSY zeolite: Alternative propargylation or allenylation of arenes, and synthesis of furan-2-ones
Devleshova, Natalia A.,Lozovskiy, Stanislav V.,Vasilyev, Aleksander V.
, (2019/08/27)
Reactions of alkyl 4-aryl(or 4,4-diaryl)-4-hydroxybut-2-ynoates [Ar(H or Ar')(OH)C4–C3≡C2–CO2Alk] with arenes under the action of triflic acid TfOH or HUSY zeolite result in the formation of two main compounds, aryl substituted furan-2-ones or products of propargylation of electron rich arenes. Key reactive intermediates in these transformations are the corresponding O,O-diprotonated forms of starting butynoates, Ar(H or Ar')(+OH2)C4–C3≡C2– C(=O+H)(OAlk), dehydration of which gives rise to mesomeric propargyl-allenyl cations Ar(H or Ar')(OH)4C+–C3≡C2–C(=O+H)(OAlk) ? Ar(H or Ar')(OH)4C = C3 = 2C+–C(=O+H)(OAlk), having two electrophilic centers on the carbons C4 and C2 respectively. Reactions of these species with arenes at C4 lead to products of arene propargylation, alternatively, reactions at C2 result in allenylation of arenes, followed by further transformation into furan-2-ones. Using quantum chemical calculations by the DFT method, it has been shown that the reactivity of such propargyl-allenyl cations is mainly explained by orbital factors. Plausible reaction mechanism is discussed.
Tellurium in organic synthesis: synthesis of bioactive butenolides
Bassora, Bruno K.,Da Costa, Carlos E.,Gariani, Rogério A.,Comasseto, Jo?o V.,Dos Santos, Alcindo A.
, p. 1485 - 1487 (2008/02/02)
Reduction of (Z)-β-butyltelluro-enones gives the corresponding γ-hydroxy vinylic tellurides with retention of the double bond configuration. Reaction of γ-hydroxy vinylic tellurides with 2 equiv of n-butyllithium produces 1,4-C,O-dianions, which on reaction with carbon dioxide give the corresponding butenolides.
Cyclohydrocarbonylation of substituted alkynes and tandem cyclohydrocarbonylation-CO insertion of α-keto alkynes catalyzed by immobilized Co-Rh heterobimetallic nanoparticles
Park, Kang Hyun,Kim, So Yeon,Chung, Young Keun
, p. 395 - 398 (2007/10/03)
The use of cobalt-rhodium (Co2Rh2) heterobimetallic nanoparticles in the cyclohydrocarbonylation of substituted alkynes and tandem cyclohydrocarbonylation-CO insertion of α-keto alkynes to give 2(3H)- or 2(5/7)-furanones is described
Conversion of 3-aryl-5-phenyl-2(3H)-furanones into 3(2H)-isothiazolone derivatives
Derbala, Hamed A.,Hamad, Abdel-Sattar S.,El Said, Waleed A.,Hashem, Ahmed I.
, p. 153 - 162 (2007/10/03)
Upon heating 3-aryl-5-phenyl-2(3H)-furanones (1a-C) with benzylamine at 100°C in the absence of solvents, ring opening occurred with the formation of the corresponding N-benzylamides (3a-c). When the latter compounds (3a-c) were allowed to react with thionyl chloride at room temperature, lhe corresponding isothiazolones (4a-c) were obtained. Treatment of the isothiazolones (4a-c) with sodium hydroxide in benzene at room temperature affected debenzoylation to give the corresponding 2-benzyl-4-aryl-3(2H)-isothiazolones (5a-c).
Chemo- and regioselective cyclohydrocarbonylation of α-keto alkynes catalyzed by a zwitterionic rhodium complex and triphenyl phosphite
Van den Hoven,El Ali,Alper
, p. 4131 - 4137 (2007/10/03)
α-Keto alkynes react with CO and H2 in the presence of catalytic quantities of the zwitterionic rhodium complex (η6-C6H5BPh3)- Rh+(1,5-COD) and triphenyl phosphite affording eith
