959860-67-4Relevant academic research and scientific papers
Regioselective Bismuth-Catalyzed Synthesis of Pyranocoumarins and Furocoumarins from 4-Hydroxycoumarins and Propargyl Alcohols
Kim, Jaehyun,Lee, Kooyeon,Lee, Phil Ho
, p. 709 - 718 (2020/07/23)
An efficient method for the bismuth-catalyzed regioselective synthesis of pyranocoumarins and furocoumarins has been developed from the reaction of 4-hydroxycoumarins with propargyl alcohols. The reaction proceeds through sequential propargylation and int
Al(OTf)3-Catalyzed Preparation of 4-Hydroxy-3-propargylic Coumarins and Subsequent Regioselective Cyclization towards Furo- or Pyrano[3,2-c]coumarins
Ponra, Sudipta,Gohain, Mukut,Van Tonder, Johannes H.,Bezuidenhoudt, Barend C.B.
supporting information, p. 745 - 750 (2015/03/30)
An efficient and economical approach to functionalized furo[3,2-c]coumarin and pyrano[3,2-c]coumarin derivatives has been developed from 4-hydroxy-3-(prop-2-ynyl)coumarin derivatives through organocatalysis or metallo-organocatalysis. Selective '5-exo-dig
Condensation of propargylic alcohols with 1,3-dicarbonyl compounds and 4-hydroxycoumarins in ionic liquids (ILs)
Aridoss, Gopalakrishnan,Laali, Kenneth K.
supporting information; experimental part, p. 6859 - 6864 (2012/02/05)
Propargylic alcohols are activated toward 1,3-diketones by Lewis or Br?nsted acidic ionic liquids (ILs) without an added catalyst, but significantly better conversions are achieved with metallic triflates [in particular Sc(OTf)3 and Ln(OTf)sub
Alkylation of 1,3-dicarbonyl compounds with benzylic and propargylic alcohols using Ir-Sn bimetallic catalyst: Synthesis of fully decorated furans and pyrroles
Chatterjee, Paresh Nath,Roy, Sujit
experimental part, p. 4569 - 4577 (2011/07/08)
The heterobimetallic complex [Ir(COD)(SnCl3)Cl(μ-Cl)] 2 catalyzes the direct substitution of hydroxyl groups in benzylic and propargylic alcohols by 1,3-dicarbonyl moiety. In 4-hydroxycoumarin, benzylation and propargylation occurs at the 3-position. Selective propargylation or allenylation takes place depending on the nature of propargylic alcohol. By applying the methodology, multi-substituted furans and pyrroles have been synthesized in good yields.
Inexpensive and efficient synthesis of propargylic substituted active methylene compounds catalyzed by FeCl3
Maiti, Sukhendu,Biswas, Srijit,Jana, Umasish
scheme or table, p. 243 - 254 (2011/03/21)
A highly efficient and practical method for the synthesis of propargylic substituted 1,3-dicarbonyl compounds with direct use of propargylic alcohols in the presence of inexpensive and environmentally benign FeCl3 (5mol%) has been presented. Th
Tris(pentafluorophenyl)borane-catalyzed alkylation of 1,3-dicarbonyl compounds with benzylic alcohols: Access to oxygenated heterocycles
Reddy, Chada Raji,Vijaykumar, Jonnalagadda,Gree, Rene
experimental part, p. 3715 - 3723 (2010/12/19)
Tris(pentafluorophenyl)borane has found to be an effective catalyst for the alkylation of 1,3-dicarbonyl compounds using benzylic alcohols as alkylating agents. Various 1,3-dicarbonyl compounds reacted cleanly with different benzylic alcohols to provide t
Molecular iodine-catalyzed C3-alkylation of 4-hydroxycoumarins with secondary benzyl alcohols
Lin, Xufeng,Dai, Xixiang,Mao, Zhenjun,Wang, Yanguang
experimental part, p. 9233 - 9237 (2010/01/16)
A highly efficient method for the C-C bond formation via molecular iodine-catalyzed C3-alkylation reaction of 4-hydroxycoumarins with benzylic, benzhydrylic, allylic, and propargyl alcohols at 50 °C in MeNO2 is described. The 3-alkylated-4-hydr
Solid-supported acid-catalyzed C3-alkylation of 4-hydroxycoumarins with secondary benzyl alcohols: access to 3,4-disubstituted coumarins via Pd-coupling
Reddy, Ch. Raji,Srikanth,Narsimha Rao,Shin, Dong-Soo
experimental part, p. 11666 - 11672 (2009/04/11)
An efficient and operationally simple method for C3-alkylation of 4-hydroxycoumarins has been developed under acidic medium giving good yields of the products. In the present method, a reusable Amberlite IR-120 (H+ form) was used as an acid catalyst and secondary benzyl alcohols were used as alkylating agents. The obtained 3-alkylated-4-hydroxycoumarins offered an easy access for the synthesis of 3,4-disubstituted coumarins by way of Pd-catalyzed coupling reactions.
Yb(OTf)3-catalyzed propargylation and allenylation of 1,3-dicarbonyl derivatives with propargylic alcohols: one-pot synthesis of multi-substituted furocoumarin
Huang, Wen,Wang, Jialiang,Shen, Quansheng,Zhou, Xigeng
, p. 11636 - 11643 (2008/03/13)
A highly efficient and mild Lewis acid-catalyzed coupling reaction of 1,3-dicarbonyl compounds with propargylic alcohols has been established. Selective propargylation or allenylation products are obtained depending on the nature of propargylic alcohols.
