[3+2] Cycloaddition reactions of 1-substituted 3,3,3-trifluoropropenes with diazo compounds and nitrilimines – synthesis of pyrazolines and pyrazoles

2022 ◽  
Author(s):  
Yuriy N. Маrkitanov ◽  
Vadim М. Тimoshenko ◽  
Sergiy S. Мykhaylychenko ◽  
Eduard B. Rusanov ◽  
Alexandr I. Khyzhan ◽  
...  
Keyword(s):  
Diazo Compounds ◽  
Cycloaddition Reactions

scholarly journals Base mediated 1,3-dipolar cycloaddition of α-substituted vinyl phosphonates with diazo compounds for synthesis of 3-pyrazolylphosphonates and 5-pyrazolcarboxylates

2016 ◽  
Vol 14 (42) ◽  
pp. 10000-10010 ◽  
Author(s):  
Nataliya S. Goulioukina ◽  
Nikolay N. Makukhin ◽  
Egor D. Shinkarev ◽  
Yuri K. Grishin ◽  
Vitaly A. Roznyatovsky ◽  
...  
Keyword(s):  
Diazo Compounds ◽  
Dipolar Cycloaddition ◽  
Cycloaddition Reactions ◽  
Vinyl Phosphonates

1-Substituted vinylphosphonates could serve as convenient precursors for functionalized pyrazoles in condition-controlled 1,3-dipolar cycloaddition reactions.

Aziridinyl imines in organic synthesis: Development of tandem reaction strategies and application to total synthesis of natural products

2013 ◽  
Vol 85 (4) ◽  
pp. 741-753 ◽  
Author(s):  
Hee-Yoon Lee ◽  
Seog-Beom Song ◽  
Taek Kang ◽  
Yoon Jung Kim ◽  
Su Jeong Geum
Keyword(s):  
Natural Products ◽  
Total Synthesis ◽  
Organic Synthesis ◽  
Reactive Intermediates ◽  
Diazo Compounds ◽  
Tandem Reaction ◽  
Cycloaddition Reactions ◽  
Free Radical Reactions ◽  
Sulfur Ylide ◽  
Epoxide Formation

Aziridinyl imines are well-known carbene equivalents because they are precursors of diazo compounds from which reactive intermediates can be produced. These carbene equivalents can be utilized as zwitterionic species, diradicals, or 4π system for cycloaddition reactions. Thus, the intermediates derived from aziridinyl imines have been used in the sulfur-ylide-mediated epoxide formation, tandem free-radical reactions, or cyclopropanation reaction via carbene intermediates to form trimethylenemethane (TMM) diyls, which undergo [2 + 3] cycloaddition reactions to form cyclopentanoids. Diazo compounds generated from aziridinyl imines also react with allenes to form TMM diyls. This reaction was utilized in tandem cycloaddition reactions of linear substrates to form polyquinanes. These tandem reaction strategies were successfully applied to the total synthesis of various cyclopentanoid natural products.

scholarly journals The Power of Iron Catalysis in Diazo Chemistry

Synthesis ◽  
2020 ◽  
Vol 53 (01) ◽  
pp. 79-94
Author(s):  
Thierry Ollevier ◽  
Virginie Carreras ◽  
Nour Tanbouza
Keyword(s):  
Short Review ◽  
Metal Catalysts ◽  
Diazo Compounds ◽  
Cycloaddition Reactions ◽  
Insertion Reactions ◽  
Iron Catalysis ◽  
Recent Advances ◽  
Olefination Reactions

AbstractThe use of iron catalysis to enable reactions with diazo compounds has emerged as a valuable tool to forge carbon–carbon or carbon–heteroatom bonds. While diazo compounds are often encountered with toxic and expensive metal catalysts, such as Rh, Ru, Pd, Ir, and Cu, a resurgence of Fe catalysis has been observed. This short review will showcase and highlight the recent advances in iron-mediated reactions of diazo compounds.1 Introduction2 Insertion Reactions2.1 Insertion into B–H Bonds2.2 Insertion into Si–H Bonds2.3 Insertion into N–H Bonds2.4 Insertion into S–H bonds3 Ylide Formation and Subsequent Reactions3.1 Doyle–Kirmse Rearrangement3.2 [1,2]-Stevens and Sommelet–Hauser Rearrangements3.3 Olefination Reactions3.4 Cycloaddition Reactions3.5 gem-Difluoroalkenylation4 Three-Component Reactions5 Miscellaneous6 Conclusion

scholarly journals [2 + 1] Cycloaddition reactions of fullerene C60 based on diazo compounds

2021 ◽  
Vol 17 ◽  
pp. 630-670
Author(s):  
Yuliya N Biglova
Keyword(s):  
Fullerene C60 ◽  
Common Variant ◽  
Present Review ◽  
Diazo Compounds ◽  
Cycloaddition Reactions ◽  
Optimal Conditions ◽  
Practical Application ◽  
Thermal Addition

The most common variant of fullerene core functionalization is the [2 + 1] cycloaddition process. Of these, reactions leading to methanofullerenes are the most promising. They are synthesized in two main reactions: nucleophilic cyclopropanation according to the Bingel method and thermal addition of diazo compounds. This present review summarizes the material on the synthesis of monofunctionalized methanofullerenes – analogues of [60]PCBM – based on various diazo compounds. The main cyclopropanating agents for the synthesis of monosubstituted methanofullerenes, the optimal conditions and the mechanism of the [2 + 1] cycloaddition, as well as the practical application of the target products are analyzed.

Tandem Cycloaddition Reactions of Allenyl Diazo Compounds Forming Triquinanes via Trimethylenemethane Diyls

2011 ◽  
Vol 133 (45) ◽  
pp. 18050-18053 ◽  
Author(s):  
Taek Kang ◽  
Won-Yeob Kim ◽  
Yeokwon Yoon ◽  
Byung Gyu Kim ◽  
Hee-Yoon Lee
Keyword(s):  
Diazo Compounds ◽  
Cycloaddition Reactions

ChemInform Abstract: Tandem Cycloaddition Reactions of Allenyl Diazo Compounds Forming Triquinanes via Trimethylenemethane Diyls.

ChemInform ◽  
2012 ◽  
Vol 43 (18) ◽  
pp. no-no
Author(s):  
Taek Kang ◽  
Won-Yeob Kim ◽  
Yeokwon Yoon ◽  
Byung Gyu Kim ◽  
Hee-Yoon Lee
Keyword(s):  
Diazo Compounds ◽  
Cycloaddition Reactions

Recent Developments in the Synthetic Uses of Silyl-protected Enoldiazoacetates for Heterocyclic Syntheses

2014 ◽  
Vol 67 (3) ◽  
pp. 365 ◽  
Author(s):  
Xinfang Xu ◽  
Michael P. Doyle
Keyword(s):  
Heterocyclic Compounds ◽  
Biologically Active Compounds ◽  
Biologically Active ◽  
Diazo Compounds ◽  
Cycloaddition Reactions ◽  
Insertion Reactions ◽  
Active Compounds ◽  
The Core ◽  
Recent Developments ◽  
Metal Catalyzed

Diazo compounds have been used as precursors to a wide variety of heterocyclic compounds that represent the core structural subunits in many biologically active compounds. Various methodologies have been established for their synthesis via metal-catalyzed carbene transformations. Although the advantages of vinyldiazoacetates have been known for many years, realization of the synthetic use of enoldiazoacetates has been more recent. This review covers advances in the utility of silyl-protected enoldiazoacetates in heterocycle syntheses that include X–H insertion reactions, ylide rearrangements, formal [3+3]- and [4+3]-cycloaddition reactions, and other traditional and unusual metal carbene transformations.

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