20473-07-8Relevant academic research and scientific papers
Convenient synthesis of spiroindolenines from tryptamine-derived isocyanides and organic azides by cobalt catalysis in pure water
Jiang, Shuai,Cao, Wen-Bin,Li, Hai-Yan,Xu, Xiao-Ping,Ji, Shun-Jun
, p. 2619 - 2623 (2021)
A Co-catalyzed coupling of 3-(2-isocyanoethyl)indoles with organic azides in pure water for accessing spiroindolenine derivatives was developed. This strategy features mild reaction conditions, high atom-economy, excellent yields, wide substrate scopes, and broad functional group tolerance. The products were obtained simply by sequential operation involving extraction, concentration, precipitation, and filtration, without tedious column chromatography. More importantly, the aqueous catalytic system could be recycled at least ten times without reducing the catalytic activity. The strategy provides a green and efficient method for the construction of spiroindolenine derivatives.
Iridium(III)-Catalyzed Selective and Mild C-H Amidation of Cyclic N-Sulfonyl Ketimines with Organic Azides
Maraswami, Manikantha,Chen, Gang,Loh, Teck-Peng
supporting information, p. 416 - 421 (2017/11/13)
A general protocol for iridium catalyzed direct C?H amidation of cyclic N-sulfonyl ketimines using sulfonyl, acyl and aryl azides as nitrogen source is reported herein. The reaction takes place at room temperature with acyl and aryl azides, while an elevated temperature needed with sulfonyl azides to furnish aminated sultams in excellent yields with complete chemo and regioselectivity, thus providing a robust and environmentally benign process to the synthesis of aminosultams. (Figure presented.).
N-Sulfonyl amidine synthesis via three-component coupling reaction using heterogeneous copper catalyst derived from metal-organic frameworks
Kim, Myeong Jin,Kim, Bo Ram,Lee, Chang Yeon,Kim, Jinho
supporting information, p. 4070 - 4073 (2016/08/18)
Three-component coupling reaction of terminal alkyne, sulfonyl azide, and amine for the synthesis of N-sulfonyl amidine was developed using heterogeneous Cu@C catalyst, which was generated by pyrolysis of HKUST-1 (Cu3(BTC)2, BTC?=?1,
Cu-catalyzed multicomponent polymerization to synthesize a library of poly(N -sulfonylamidines)
Lee, In-Hwan,Kim, Hyunseok,Choi, Tae-Lim
supporting information, p. 3760 - 3763 (2013/04/24)
We report a versatile Cu-catalyzed multicomponent polymerization (MCP) technique that enables the synthesis of high-molecular-weight, defect-free poly(N-sulfonylamidines) from monomers of diynes, sulfonyl azides, and diamines. Through a series of optimizations, we discovered that the addition of excess triethylamine and the use of N,N′-dimethylformamide as a solvent are key factors to ensure efficient MCP. Formation of cyclic polyamidines was a side reaction during polymerization, but it was readily controlled by using diynes or diamines with long or rigid moieties. In addition, this polymerization is highly selective for three-component reactions over click reactions. The combination of the above factors enables the synthesis of high-molecular-weight polymers, which was challenging in previous MCPs. All three kinds of monomers (diynes, sulfonyl azides, and diamines) are readily accessible and stable under the reaction conditions, with various monomers undergoing successful polymerization regardless of their steric and electronic properties. Thus, we synthesized various high-molecular-weight, defect-free polyamidines from a broad range of monomers while overcoming the limitations of previous MCPs, such as low conversion and defects in the polymer structures.
Ru(ii)-catalyzed intermolecular ortho-C-H amidation of aromatic ketones with sulfonyl azides
Bhanuchandra,Ramu Yadav,Rit, Raja K.,Rao Kuram, Malleswara,Sahoo, Akhila K.
supporting information, p. 5225 - 5227 (2013/06/27)
Ru(ii)-catalyzed intermolecular ortho-C-H amidation of weakly coordinating aromatic ketones with sulfonyl azides is reported. The developed reaction protocol can be extended to various substituted aromatic ketones to afford a wide range of desired C-N bond formation products in good yields.
Synthesis of sulfonyl azides
Katritzky, Alan,Widyan, Khalid,Gyanda, Kapil
, p. 1201 - 1204 (2008/12/22)
1-(Alkylsulfonyl)- and 1-(arylsulfonyl)benzotriazoles react with sodium azide in acetonitrile to give the corresponding alkanesulfonyl and arenesulfonyl azides. Georg Thieme Verlag Stuttgart.
