33685-12-0Relevant articles and documents
Indium-mediated propargylation of imines and imine oxides in aqueous media: Propargylation of >C=N- centres
Prajapati, Dipak,Laskar, Dhrubojyoti D.,Gogoi, Baikuntha J.,Devi, Gitali
, p. 6755 - 6757 (2003)
The indium-catalysed coupling of propargyl bromide with a variety of imines and imine oxides afforded the corresponding propargylated products in high yields under mild conditions.
Povarov Reaction of Cycloiminium Formed in Situ via Hydroamination Cycloisomerization of Homopropargylic Amines with Electron-Rich Olefins
Liu, Qiangqiang,Wang, Chan,Li, Qiang,Hou, Yajie,Wu, Ye,Liu, Lingyan,Chang, Weixing,Li, Jing
, p. 950 - 958 (2017)
A new, one-pot cascade reaction of homopropargylic amines with electron-rich olefins is developed in the presence of Cu(OTf)2 and affords a series of octahydrofuro[3,2-c]pyrrolo[1,2-a]quinoline derivatives in yields of 38-80%. This reaction pro
The Diverse Reactivity of Homopropargylic Amines as “Masked” 1C Synthons for the Aza-Friedel–Crafts Alkylation of Indoles
Chen, Hao,Ni, Min,Bao, Xiaofeng,Wang, Chan,Liu, Lingyan,Chang, Weixing,Li, Jing
supporting information, p. 470 - 476 (2018/02/09)
A novel type of “masked” 1C synthon was developed through the hydroamination cyclization-protonation of homopropargylic amines to act as aza-Friedel–Crafts alkylation reagents to react with indoles. A variety of 3-(2-pyrrolidinyl)indoles were generated in good to high yields. More significantly, some of the corresponding products display potential bioactivity against chlamydial infection, wherein they specifically target the mid-stage of the chlamydial life cycle by interfering with RB replication.
The Divergent Cascade Reactions of Arylalkynols with Homopropargylic Amines or Electron-Deficient Olefins: Access to the Spiro-Isobenzofuran- b-pyrroloquinolines or Bridged-Isobenzofuran Polycycles
Wang, Lun,Liu, Lingyan,Chang, Weixing,Li, Jing
supporting information, p. 7799 - 7813 (2018/06/18)
Two divergent cascade reactions of arylalkynols with homopropargylic amines or electron-deficient olefins were developed to synthesize the spiro-isobenzofuran-b-pyrroloquinolines or bridged-isobenzofuran heterocycles in good yields, respectively. One reaction actually involved intramolecular 5-endo-dig hydroamination cyclization-protonation of homopropargylic amines to give cycloiminium ions and intramolecular 5-exo-dig hydroalkoxylation cyclization of arylalkynols to generate isobenzofuran with exocyclic double bond, followed by the nontypical Povarov-type reaction in the presence of PtCl2/FeCl3 cocatalysts. The other underwent intramolecular hydroalkoxylation cycloisomerization of alkynols with the subsequent normal [4 + 2] cycoaddition with dienophiles. Herein, the arylalkynols acted as both "masked" electron-rich olefins and "masked" electron-rich dienes.
Silver-Catalyzed Three-Component 1,1-Aminoacylation of Homopropargylamines: α-Additions for Both Terminal Alkynes and Isocyanides
Tong, Shuo,Piemontesi, Cyril,Wang, Qian,Wang, Mei-Xiang,Zhu, Jieping
supporting information, p. 7958 - 7962 (2017/06/27)
The reaction of secondary homopropargylamines, isocyanides, and water in the presence of a catalytic amount of silver acetate and subsequent purification by chromatography on silica gel afforded substituted proline amides in good to excellent yields. Primary homopropargylamines underwent a cyclizative Ugi–Joullié three-component reaction with isocyanides and carboxylic acids to afford functionalized N-acyl proline amides. High diastereoselectivity was observed in the synthesis of 4-alkoxy and 4,5-disubstituted proline derivatives. This work represents the first examples of a three-component cyclizative 1,1-aminoacylation of terminal alkynes.
Synthesis of Tetrasubstituted Pyrroles from Homopropargylic Amines via a Sonogashira Coupling/Intramolecular Hydroamination/Oxidation Sequence
Wang, Chan,Huang, Kaimeng,Wang, Junying,Wang, Hongkai,Liu, Lingyan,Chang, Weixing,Li, Jing
supporting information, p. 2795 - 2802 (2015/09/28)
A one-pot reaction of homopropargylic amines and aryl iodides was developed in the presence of a palladium (Pd) catalyst and generated a series of tetrasubstituted pyrrole derivatives in good to high yields. This process involved a Sonogashira, intramolecular hydroamination, cyclization and oxidation sequence of reactions.
