- One-pot, two-step synthesis of 7-methylene-1,5-piperazine-fused 1,2,3-triazoles
-
A facile, one-pot two-step synthesis of 7-methylene-1,5-piperazine-fused 1,2,3-triazole derivatives has been developed. The protocol employs an N-allylation of N-propargylated amines with 2,3-dibromopropene in the presence of K2CO3 in DMSO and a CuI-catalyzed [3 + 2] cycloaddition reaction of the synthetic N-(2-bromoallyl)-N-propargyl amines with sodium azide sequentially. Such a method provides methylene-substituted 1,2,3-triazole fused piperazines with some advantages such as simple operation, high efficiency and good product yield (80–91%) through readily available starting materials.
- Kuang, Lu,Ming, Peng,Wan, Chang-Feng,Chen, Jun-Min,Sheng, Shou-Ri
-
p. 563 - 569
(2020/11/19)
-
- Enantioselective Carboetherification/Hydrogenation for the Synthesis of Amino Alcohols via a Catalytically Formed Chiral Auxiliary
-
Chiral auxiliaries and asymmetric catalysis are the workhorses of enantioselective transformations, but they still remain limited in terms of either efficiency or generality. Herein, we present an alternative strategy for controlling the stereoselectivity of chemical reactions. Asymmetric catalysis is used to install a transient chiral auxiliary starting from achiral precursors, which then directs diastereoselective reactions. We apply this strategy to a palladium-catalyzed carboetherification/hydrogenation sequence on propargylic amines, providing fast access to enantioenriched chiral amino alcohols, important building blocks for medicinal chemistry and drug discovery. All stereoisomers of the product could be accessed by the choice of ligand and substituent on the propargylic amine, leading to a stereodivergent process.
- Buzzetti, Luca,Puri??, Mikus,Greenwood, Phillip D. G.,Waser, Jerome
-
supporting information
p. 17334 - 17339
(2020/11/02)
-
- Lanthanide-Catalyzed Reversible Alkynyl Exchange by Carbon–Carbon Single-Bond Cleavage Assisted by a Secondary Amino Group
-
Lanthanide-catalyzed alkynyl exchange through C?C single-bond cleavage assisted by a secondary amino group is reported. A lanthanide amido complex is proposed as a key intermediate, which undergoes unprecedented reversible β-alkynyl elimination followed by alkynyl exchange and imine reinsertion. The in situ homo- and cross-dimerization of the liberated alkyne can serve as an additional driving force to shift the metathesis equilibrium to completion. This reaction is formally complementary to conventional alkyne metathesis and allows the selective transformation of internal propargylamines into those bearing different substituents on the alkyne terminus in moderate to excellent yields under operationally simple reaction conditions.
- Shao, Yinlin,Zhang, Fangjun,Zhang, Jie,Zhou, Xigeng
-
supporting information
p. 11485 - 11489
(2016/10/24)
-
- A synthetic in alkyne endalkyne propylamine derivatives containing different substituents method of (by machine translation)
-
The invention belongs to the field of organic synthesis technology, in particular to a kind of synthetic in alkyne endalkyne propylamine derivatives containing different substituents method. This invention, through a carbon-carbon single bond of activation between alkyne propylamine the mutual conversion of different, the rare-earth catalyst system, terminal alkyne as compounds with propargyl substituted secondary amine as raw material, the preparation containing various substituents alkyne endalkyne propylamine derivatives. The method of the invention the raw material sources are widespread or easy to prepare, simple and convenient operation, selectively controllable, high yield. (by machine translation)
- -
-
Paragraph 0027
(2016/11/07)
-
- Platinum-catalyzed cyclization reaction of alkynes: Synthesis of azepino[3,4-b]indol-1-ones
-
Novel azepino[3,4-b]indol-1-ones were synthesized from alkyne-substituted indole-2-carboxamides by catalytic intramolecular cyclization in the presence of PtCl2. The scope and limitations of this straightforward protocol are reported.
- Gruit, Marina,Pews-Davtyan, Anahit,Beller, Matthias
-
experimental part
p. 1148 - 1159
(2011/04/15)
-