Warning: Undefined array key "mm" in /www/wwwroot/www.ai-bt.com/si.php on line 10 Deprecated: trim(): Passing null to parameter #1 ($string) of type string is deprecated in /www/wwwroot/www.ai-bt.com/si.php on line 10 SuFExable NH-Pyrazoles via 1,3-Dipolar Cycloadditions of Diazo Compounds with Bromoethenylsulfonyl Fluoride.

Literature DB >> 35143195

SuFExable NH-Pyrazoles via 1,3-Dipolar Cycloadditions of Diazo Compounds with Bromoethenylsulfonyl Fluoride.

Pavel Yamanushkin¹, Kemal Kaya^1,2, Mark Aldren M Feliciano¹, Brian Gold¹.

Abstract

"Click" reactions have transformed the molecular sciences. Augmenting cycloaddition reactions, sulfur(VI) fluoride exchange (SuFEx) chemistry has diversified the landscape of molecular assembly. Herein, we report a facile strategy to access SuFExable NH-pyrazoles via strain and catalyst-free 1,3-dipolar cycloadditions of stabilized diazo compounds under mild conditions. Subsequent SuFEx proceeds efficiently with various N- and O-nucleophiles. Access to SuFExable NH-pyrazoles─a class of compounds containing two common pharmacophores─enables future opportunities within drug discovery, chemical biology, materials chemistry, and related fields.

Entities: Chemical

Mesh：

Substances：

Year: 2022 PMID： 35143195 PMCID： PMC9011340 DOI： 10.1021/acs.joc.1c03105

Source DB: PubMed Journal: J Org Chem ISSN： 0022-3263 Impact factor: 4.198

69 in total

1. Novel N-transfer reagent for converting α-amino acid derivatives to α-diazo compounds.

Authors: Guan-Han Lu; Tzu-Chia Huang; Hsiao-Chin Hsueh; Shin-Cherng Yang; Ting-Wei Cho; Ho-Hsuan Chou
Journal: Chem Commun (Camb) Date: 2021-04-19 Impact factor: 6.222

2. Metal-Free Synthesis of Functional 1-Substituted-1,2,3-Triazoles from Ethenesulfonyl Fluoride and Organic Azides.

Authors: Marie-Claire Giel; Christopher J Smedley; Emily R R Mackie; Taijie Guo; Jiajia Dong; Tatiana P Soares da Costa; John E Moses
Journal: Angew Chem Int Ed Engl Date: 2019-11-28 Impact factor: 15.336

3. 1,3-Dipolar Cycloadditions of Diazo Compounds in the Presence of Azides.

Authors: Matthew R Aronoff; Brian Gold; Ronald T Raines
Journal: Org Lett Date: 2016-03-16 Impact factor: 6.005

4. Sulfur(VI) fluoride exchange (SuFEx): another good reaction for click chemistry.

Authors: Jiajia Dong; Larissa Krasnova; M G Finn; K Barry Sharpless
Journal: Angew Chem Int Ed Engl Date: 2014-08-11 Impact factor: 15.336

5. Alkynyl crown ethers as a scaffold for hyperconjugative assistance in noncatalyzed azide-alkyne click reactions: ion sensing through enhanced transition-state stabilization.

Authors: Brian Gold; Paratchata Batsomboon; Gregory B Dudley; Igor V Alabugin
Journal: J Org Chem Date: 2014-06-20 Impact factor: 4.354

6. Triple, Mutually Orthogonal Bioorthogonal Pairs through the Design of Electronically Activated Sulfamate-Containing Cycloalkynes.

Authors: Yun Hu; Jessica M Roberts; Henry R Kilgore; Amirah S Mat Lani; Ronald T Raines; Jennifer M Schomaker
Journal: J Am Chem Soc Date: 2020-10-21 Impact factor: 15.419

SuFExable NH-Pyrazoles via 1,3-Dipolar Cycloadditions of Diazo Compounds with Bromoethenylsulfonyl Fluoride.

1. Novel N-transfer reagent for converting α-amino acid derivatives to α-diazo compounds.

2. Metal-Free Synthesis of Functional 1-Substituted-1,2,3-Triazoles from Ethenesulfonyl Fluoride and Organic Azides.

3. 1,3-Dipolar Cycloadditions of Diazo Compounds in the Presence of Azides.

4. Sulfur(VI) fluoride exchange (SuFEx): another good reaction for click chemistry.

5. Alkynyl crown ethers as a scaffold for hyperconjugative assistance in noncatalyzed azide-alkyne click reactions: ion sensing through enhanced transition-state stabilization.

6. Triple, Mutually Orthogonal Bioorthogonal Pairs through the Design of Electronically Activated Sulfamate-Containing Cycloalkynes.

7. SuFEx Click Chemistry Enabled Late-Stage Drug Functionalization.

Review 8. Analyzing Reaction Rates with the Distortion/Interaction-Activation Strain Model.

Review 9. The Emerging Applications of Sulfur(VI) Fluorides in Catalysis.

Review 1. The 1,3-Dipolar Cycloaddition: From Conception to Quantum Chemical Design.