Generation of azomethine imine and metal-free formal 1,3-dipolar cycloaddition of imine with PhIO: reaction, scope, and synthesis

2010 ◽  
Vol 46 (12) ◽  
pp. 2022 ◽  
Author(s):  
Dilip K. Maiti ◽  
Nirbhik Chatterjee ◽  
Palash Pandit ◽  
Sandip K. Hota
Keyword(s):  
Dipolar Cycloaddition ◽  
Metal Free ◽  
Azomethine Imine

ChemInform Abstract: Generation of Azomethine Imine and Metal-Free Formal 1,3-Dipolar Cycloaddition of Imine with PhIO: Reaction, Scope, and Synthesis.

ChemInform ◽  
2010 ◽  
Vol 41 (30) ◽  
pp. no-no
Author(s):  
Dilip K. Maiti ◽  
Nirbhik Chatterjee ◽  
Palash Pandit ◽  
Sandip K. Hota
Keyword(s):  
Dipolar Cycloaddition ◽  
Metal Free ◽  
Azomethine Imine

1,3-dipolar cycloaddition in the synthesis of glycoconjugates of natural chlorins and bacteriochlorins

2009 ◽  
Vol 13 (03) ◽  
pp. 336-345 ◽  
Author(s):  
Mikhail A. Grin ◽  
Ivan S. Lonin ◽  
Anna A. Lakhina ◽  
Elena S. Ol'shanskaya ◽  
Alexey I. Makarov ◽  
...  
Keyword(s):  
Triple Bond ◽  
Tautomeric Form ◽  
Click Reaction ◽  
Copper Cation ◽  
Water Soluble ◽  
Dipolar Cycloaddition ◽  
Nmr Studies ◽  
Metal Free ◽  
Cu Complex ◽  
Derivatives Of

Glucose-, galactose- and lactose-containing photosensitizers based on derivatives of chlorophyll a and bacteriochlorophyll a were synthesized with the use of [3+2] cycloaddition between sugar azides and triple bond derivatives of chlorins and bacteriochlorins. Unlike bacteriochlorin cycloimide, chlorin was detected to form a Cu -complex during the click reaction. An approach to the synthesis of metal-free glycosylated chlorins was developed with the use of "protection" by Zn 2+ cation and subsequent demetalation. It is based on the action of alkynyl chlorin e6 derivative Zn -complex, which is resistant to the substitution by copper cation. Bacteriochlorin p cycloimide conjugate with per-acetylated β-D-lactose was obtained and shown to become water-soluble after unblocking of the lactose hydroxy functions. NMR studies allowed for the elucidation of structure, tautomeric form and conformation of the obtained compounds.

Copper-Catalyzed Azomethine Imine–Alkyne Cycloadditions (CuAIAC)

Synthesis ◽  
2018 ◽  
Vol 50 (23) ◽  
pp. 4501-4524 ◽  
Author(s):  
Jurij Svete ◽  
Uroš Grošelj ◽  
Franc Požgan ◽  
Bogdan Štefane
Keyword(s):  
Experimental Data ◽  
Click Chemistry ◽  
Organic Synthesis ◽  
Present Review ◽  
Metal Free ◽  
Azomethine Imine ◽  
Cuaac Reaction ◽  
Azomethine Imines

Although the first example of copper-catalyzed azomethine imine–alkyne cycloaddition (CuAIAC) was published only a year after the seminal papers of Meldal and Sharpless on Cu-catalyzed azide–alkyne cycloaddition (CuAAC), the CuAIAC reaction has remained overlooked by the synthetic community for almost a decade. Since 2010, however, CuAIAC reaction started to emerge as a promising supplement to the well-known CuAAC reaction. The present review surveys primarily the literature on CuAIAC reaction since 2003. Beside this, azomethine imine–alkyne cycloadditions catalyzed by other metals, selected examples of metal-free reactions, and related [3+3] and [3+4] cycloadditions of azomethine imines are presented. All these experimental data indicate the viability of CuAIAC in organic synthesis and the applicability in ‘click’ chemistry.1 Introduction2 Reactions with Acyclic Azomethine Imines3 Reactions with C,N-Cyclic Azomethine Imines4 Reactions with N,N-Cyclic Azomethine Imines5 Reactions with C,N,N-Cyclic Azomethine Imines6 The Mechanism of the CuAIAC Reaction7 Conclusions and Outlook

Photoinduced, strain-promoted cycloadditions of trans-cycloheptenones and azides

2020 ◽  
Vol 22 (20) ◽  
pp. 7023-7030
Author(s):  
Hongzhi Yang ◽  
Tianying Zeng ◽  
Shuang Xi ◽  
Shengkun Hu ◽  
Yunfei Wu ◽  
...  
Keyword(s):  
Oxidation Reaction ◽  
Aerobic Oxidation ◽  
Dipolar Cycloaddition ◽  
Reaction Sequence ◽  
Metal Free

Metal-free cycloadditions of cycloheptenones with azides have been developed, hinging on a photoisomerization/1,3-dipolar cycloaddition/aerobic oxidation reaction sequence.

scholarly journals Metal-Free Click Synthesis of Functional 1-Substituted-1,2,3-Triazoles

2019 ◽  
Author(s):  
Marie-Claire Giel ◽  
Christopher J. Smedley ◽  
Emily R. R. Mackie ◽  
Taijie Guo ◽  
Jiajia Dong ◽  
...  
Keyword(s):  
Click Reaction ◽  
Dipolar Cycloaddition ◽  
Chromatographic Purification ◽  
Metal Free ◽  
Organic Azides ◽  
Novel Method ◽  
Fluoride Salts ◽  
Sulfonyl Fluoride ◽  
Click Synthesis ◽  
Selection Of

The 1,2,3-triazole group is one of the most important connective linkers and functional aromatic heterocycles in modern chemistry. The boom in growth of, in particular, 1,4-disubstituted triazole products since the early 2000’s, can be largely attributed to the birth of click chemistry and the discovery of the Cu(I)-catalyzed azide-alkyne cycloaddition (CuAAC). Yet the synthesis of relatively simple, albeit important, 1-substituted-1,2,3-triazoles, has been surprisingly more challenging. We report a straightforward and scalable click-protocol for the synthesis of 1-substituted-1,2,3-triazoles from organic azides and the bench stable acetylene-surrogate, ethenesulfonyl fluoride (ESF). The transformation proceeds through a thermal 1,3-dipolar cycloaddition of the azide and ESF to give a sulfonyl fluoride substituted triazoline, that itself spontaneously aromatizes through formal loss of HF/SO<sub>2 </sub>to give the stable triazole products with excellent fidelity. The new click reaction tolerates a wide selection of substrates and proceeds smoothly under metal-free conditions to give the products in excellent yield, and without need for additives or chromatographic purification. Further, under controlled conditions, the 1-substituted-1,2,3-triazole products undergo Michael reaction with a second equivalent of ESF to give the unprecedented 1-substituted triazolium sulfonyl fluoride salts, demonstrating the versatility and orthogonal reactivity of ESF. The importance of this novel method is evidenced through the late-stage modification of several drugs and drug fragments, including the synthesis of a new improved derivative of the famous antibiotic, chloramphenicol.

scholarly journals 1,3-Dipolar Cycloadditions of Isatin N,N′‑Cyclic Azomethine Imines with Alkynes for the synthesis of spiro[indoline-3,1'-pyrazolo[1,2-a]pyrazoles]

2019 ◽  
Author(s):  
Yang Shi ◽  
Gangqiang Wang ◽  
Zhiyu Chen ◽  
Minghu Wu ◽  
Jian Wang ◽  
...  
Keyword(s):  
Functional Group ◽  
Biologically Active ◽  
Dipolar Cycloaddition ◽  
Dipolar Cycloadditions ◽  
Azomethine Imine ◽  
Azomethine Imines

CuCO3 catalyzed 1, 3-dipolar cycloaddition of isatin N,N′‑cyclic azomethine imine has been developed.  Biologically active heterocyclic spiro[indoline-3,1'-pyrazolo[1,2-a]pyrazoles] were prepared as single regioisomers in good yields and functional group compatibility.

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