153396-18-0Relevant academic research and scientific papers
Glyoxylic Acid: A Carboxyl Group-Assisted Metal-Free Decarboxylative Reaction Toward Propargylamines
Huang, Liliang,Xie, Yujuan,Ge, Panyuan,Huang, Junhai,Feng, Huangdi
supporting information, p. 2448 - 2451 (2021/06/28)
Readily available propargylamines are not only fundamental building blocks in organic synthesis, but also possess many prominent biological activities. A highly efficient, concise and environmentally benign decarboxylative reaction of glyoxylic acid monohydrate with secondary amines and alkynes has been elaborated, and a variety of propargylamines are delivered in moderate to good yields under metal-free conditions. A mechanism involving a carboxyl group that assists the reactivity of alkynes, which makes the procedure of Michael addition proceeded smoothly, has been proposed.
Efficient synthesis of propargylamines from terminal alkynes, dichloromethane and tertiary amines over silver catalysts
Chen, Xiuling,Chen, Tieqiao,Zhou, Yongbo,Au, Chak-Tong,Han, Li-Biao,Yin, Shuang-Feng
supporting information, p. 247 - 250 (2014/01/06)
A simple, efficient and highly functional group compatible method for the synthesis of propargylamines from terminal alkynes, dichloromethane and tertiary amines using silver catalysts has been developed.
One-pot oxidation and rearrangement of propargylamines and in situ pyrazole synthesis
Chen, Jinshan,Properzi, Roberta,Uccello, Daniel P.,Young, Jennifer A.,Dushin, Russell G.,Starr, Jeremy T.
supporting information, p. 4146 - 4149 (2014/09/29)
Reported here are procedures for a one-pot oxidation and rearrangement of propargylamines to synthesize enaminones, with supporting mechanistic studies. Also reported are the extended one-pot syntheses of pyrazoles, including celecoxib and various heterocyclic compounds.
Nickel-catalyzed three-component coupling reaction of terminal alkynes, dihalomethane and amines to propargylamines
Lanke, Satish R.,Bhanage, Bhalchandra M.
, p. 729 - 733 (2013/12/04)
Direct C - H and C - halogen activation is an important and practical task in C - C, C - N bond formation reactions using alkynes. Propargylic amines are synthetically versatile intermediates for the preparation of many nitrogen-containing biologically ac
Bridging homogeneous and heterogeneous catalysis with MOFs: Cu-MOFs as solid catalysts for three-component coupling and cyclization reactions for the synthesis of propargylamines, indoles and imidazopyridines
Luz,Llabres I Xamena,Corma
scheme or table, p. 285 - 291 (2012/02/15)
Copper-containing MOFs are found to be active, stable and reusable solid catalysts for three-component couplings of amines, aldehydes and alkynes to form the corresponding propargylamines. Two tandem reactions, including an additional cyclization step, le
Alkynylation of aryl bromides with propargylamines catalyzed by a palladium-tetraphosphine complex
Lemhadri, Mhamed,Doucet, Henri,Santelli, Maurice
, p. 1359 - 1367 (2007/10/03)
The tetraphosphine all-cis-1,2,3,4-tetrakis(diphenylphosphinomethyl) cyclopentane in combination with [Pd(C3H5)Cl]2 affords a very efficient catalyst for the alkynylation of aryl bromides with propargylamines. Higher reactions rates were observed with N,N- dialkylpropargylamines than with N-methylpropargylamine or propargy lamine. A wide variety of substituents such as alkyl, phenyl, methoxy, dimethylamino, fluoro, trifluoromethyl, acetyl, benzoyl, formyl, carboxylate, nitro, or nitrile, on the aryl bromides are tolerated. High turnover numbers can be obtained with most of these aryl bromides. The coupling reaction of sterically very congested aryl bromides such as 9-bromoanthracene or 2,4,6- triisopropylbromobenzene also proceeds in good yields. Georg Thieme Verlag Stuttgart.
