scholarly journals The Reactivity of Azidonitrobenzofuroxans towards 1,3-Dicarbonyl Compounds: Unexpected Formation of Amino Derivative via the Regitz Diazo Transfer and Tautomerism Study

2021 ◽  
Vol 22 (17) ◽  
pp. 9646
Author(s):  
Elena Chugunova ◽  
Almir Gazizov ◽  
Daut Islamov ◽  
Alexander Burilov ◽  
Alena Tulesinova ◽  
...  
Keyword(s):  
Carbonyl Compounds ◽  
Amino Derivative ◽  
Dipolar Cycloaddition ◽  
Unexpected Formation ◽  
Strong Electron ◽  
Dicarbonyl Compounds

Herein, we report on the reaction of nitro-substituted azidobenzofuroxans with 1,3-dicarbonyl compounds in basic media. The known reactions of benzofuroxans and azidofuroxans with 1,3-dicarbonyl compounds in the presence of bases are the 1,3-dipolar cycloaddition and the Beirut reaction. In contrast with this, azidonitrobenzofuroxan reacts with 1,3-carbonyl compounds through Regitz diazo transfer, which is the first example of this type of reaction for furoxan derivatives. This difference is seemingly due to the strong electron-withdrawing effect of the superelectrophilic azidonitrobenzofuroxan, which serves as the azido transfer agent rather than 1,3-dipole in this case.

The 1,3-Dipolar Cycloaddition Reactions of Nitrile Oxides in Water Media

2021 ◽  
Vol 25 ◽  
Author(s):  
Joaquín Plumet
Keyword(s):  
Carbonyl Compounds ◽  
Critical Discussion ◽  
Aldol Reactions ◽  
Dipolar Cycloaddition ◽  
Hydroxy Ketone ◽  
Unsaturated Ketones ◽  
Dipolar Cycloadditions ◽  
Nitrile Oxides ◽  
Water Media ◽  
Synthetic Intermediates

: The 1,3-dipolar cycloadditions (DCs) of nitrile oxides (NOs) have been used as a powerful tool in synthetic organic chemistry. The cycloadducts arising from cycloadditions (CAs) of NOs to alkenes and alkynes (2-isoxazolines and isoxazoles respectively) are valuable synthetic intermediates because, among others, their capacity to mask other functionalities including α, β-unsaturated ketones, β-hydroxy carbonyl compounds and 1,3-aminoalcohols. In particular, the β-hydroxy ketone functionality is an illustrative example, making the NOs alkenes CAs reactions a synthetically equivalent methodology of aldol reactions. The vast majority of these reactions are carried out in organic solvents. Nevertheless, the use of water as an alternative solvent has evident advantages on the “Green Chemistry” concept. The critical discussion on the use of water instead of “conventional” solvents in the 1,3-DCs reactions of NOs is the objective of the present review.

Synthesis of Phenyl-2,2′-bichalcophenes and Their Aza-Analogues by Catalytic Oxidative Deacetylation

Synthesis ◽  
2019 ◽  
Vol 51 (17) ◽  
pp. 3259-3268
Author(s):  
Xia Jiang ◽  
Hui Jin ◽  
Tingshu Wang ◽  
Hyebin Yoo ◽  
Sangho Koo
Keyword(s):  
Ethyl Acetoacetate ◽  
Carbonyl Compounds ◽  
Conjugate Addition ◽  
Synthetic Method ◽  
Dicarbonyl Compounds

Efficient synthetic method for medicinally and opto-electronically important bichalcophenes is reported, which highlights Mn(OAc)3/CoCl2-catalyzed oxidative deacetylation of 1,5-dicarbonyl compounds that were easily prepared by conjugate addition of ethyl acetoacetate to α,β-unsaturated carbonyl compounds containing a chalcophene unit. Paal–Knorr reaction of the resulting 1,4-dicarbonyl compounds produced 4-phenyl-2,2′-bichalcophenes and their aza-analogues.

Utilization of electron-donating α,β-unsaturated oximes: regioselective inverse 1,3-dipolar cycloaddition of nitrones

2017 ◽  
Vol 53 (18) ◽  
pp. 2685-2688 ◽  
Author(s):  
Yoshimitsu Hashimoto ◽  
Hiromasa Ishiwata ◽  
Soko Tachikawa ◽  
Shintaro Ban ◽  
Nobuyoshi Morita ◽  
...  
Keyword(s):  
Carbonyl Compounds ◽  
Dipolar Cycloaddition

The cycloaddition of nitrones with α,β-unsaturated carbonyl compounds (enones) afforded predominantly 4-acylisoxazolidines, whereas the cycloaddition of the corresponding oximes afforded 5-iminoisoxazolidines.

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