1195757-35-7Relevant academic research and scientific papers
Dynamic Kinetic Resolution in Gold-Catalyzed (4 + 2)-Annulations between Alkynyl Benzaldehydes and Allenamides to Yield Enantioenriched All-Carbon Diarylalkylmethane Derivatives
Pandit, Yashwant Bhaskar,Liu, Rai-Shung
supporting information, p. 548 - 553 (2022/01/20)
This work reports the synthesis of diarylmethane derivatives via gold-catalyzed (4 + 2)-annulations between alkynyl benzaldehydes and allenamides, followed by an aza-Claisen rearrangement. Deuterium labeling and crossover experiments have been performed to confirm this proposed mechanism. With racemic 3-substituted allenamides in a substrate ratio (1:1), we employ chiral gold catalysts to achieve a dynamic kinetic resolution to obtain enantioenriched diarylalkylmethane derivatives with high e.r. levels (up to 93:7).
Iron-Mediated Cyclization of 1,3-Diynyl Propargyl Aryl Ethers with Dibutyl Diselenide: Synthesis of Selenophene-Fused Chromenes
Back, Davi F.,Lutz, Guilherme,Zeni, Gilson
, p. 1096 - 1105 (2020/01/25)
The synthesis of selenophene-fused chromene derivatives starting from 1,3-diynyl propargyl aryl ethers is reported herein. The method is based on carbon-carbon, carbon-selenium, selenium-carbon and carbon-selenium bonds formation in a one-pot protocol, using iron(III) chloride and dibutyl diselenide as promoters. The same reaction conditions were applied to propargyl anilines leading to the formation of 1-(butylselanyl)-selenophene quinolines. The results showed that the dilution and temperature of substrate addition had a crucial influence in the products obtained. When the substrates were added at room temperature, in the absence of a solvent, a mixture of products was obtained, whereas the slowly addition (15 min) of starting materials, as a dichloromethane solution, at 0 °C led to the product formation in good yields. The mechanistic study indicates that the cooperative action between iron(III) chloride and dibutyl diselenide was essential to promote the cyclization, whereas separately none of them was effective in promoting the cyclization. We proved the synthetic utility of heterocycles obtained in the Suzuki cross coupling reaction, giving the corresponding cross-coupled products in good yields. In addition, the organoselenium moiety was removed from the structures of products by using n-butyllithium. (Figure presented.).
[3+2]-Annulation of platinum-bound azomethine ylides with distal C=C bonds of N-allenamides
Chakrabarty, Indradweep,Inamdar, Suleman M.,Akram, Manjur O.,Gade, Amol B.,Banerjee, Subhrashis,Bera, Saibal,Patil, Nitin T.
supporting information, p. 196 - 199 (2016/12/27)
A Pt-catalyzed, highly regioselective reaction between N-allenamides and imino-alkynes leading to pyrrolo[1,2-a]indoles is described. This represents the first example of [3+2]-annulation of Pt-bound azomethine ylides with the distal C=C bond of N-allenam
Intramolecular annulation of aromatic rings with N-sulfonyl 1,2,3-triazoles: Divergent synthesis of 3-methylene-2,3-dihydrobenzofurans and 3-methylene-2,3-dihydroindoles
Tang, Xiang-Ying,Zhang, Yong-Sheng,He, Lv,Wei, Yin,Shi, Min
supporting information, p. 133 - 136 (2015/01/09)
The controllable synthesis of 3-methylene-2,3-dihydrobenzofurans 2 and 3-methylene-2,3-dihydroindoles 5 has been developed through Rh-catalyzed intramolecular annulation of aromatic rings with azavinyl carbenes. This journal is
Synthesis of substituted quinolines from N-aryl-N-(2-alkynyl) toluenesulfonamides via FeCl3-mediated intramolecular cyclization and concomitant detosylation
Roy,Ansary, Inul,Samanta, Srikanta,Majumdar
scheme or table, p. 5119 - 5122 (2012/09/25)
A series of substituted quinolines have been synthesized in moderate to good yields (55-81%) from easily available substrates N-aryl-N-(2-alkynyl) toluenesulfonamides via FeCl3-mediated intramolecular cyclization and concomitant detosylation.
The Au(I)-catalyzed intramolecular hydroarylation of terminal alkynes under mild conditions: Application to the synthesis of 2H-chromenes, coumarins, benzofurans, and dihydroquinolines
Menon, Rajeev S.,Findlay, Alison D.,Bissember, Alex C.,Banwell, Martin G.
supporting information; experimental part, p. 8901 - 8903 (2010/03/01)
(Chemical Equation Presented) Operationally simple Au(I)-catalyzed intramolecular hydroarylation (IMHA) reactions of terminal alkynes that proceed in high yield and under very mild conditions are described. These processes involve low catalyst loadings, mild reaction temperatures, and short reaction times, require no cocatalysts or additives, and allow for the generation of a number of important heterocyclic motifs from readily accessible starting materials.
