Eco-Friendly Approach to Tetrasubstituted Diazodihydrofuran­ones: Valuable Precursors of Oxetane Derivatives and Other Heterocyclic Compounds

Benzophenone-sensitizedr eactions of 4-diazotetrahydrofuran-3(2H)-onesw ith H-donors such as tetrahydrofuran, 1,4-dioxane,c yclohexane and diethyle ther,o ccur without elimination of nitrogen and give rise to the corresponding N-substituted hydrazones or bis-hydrazonoethanes due to af ormal insertion of the terminal Natom of diazo group into a-CÀHb onds of ethers and aliphatic hydrocar-bons, with yields of up to 78 %. Long-wavelength UV irradiation (l > 310 nm) is most suitable fort his process, whereas oxygen molecules adequately quench the triplet excited state of the diazoketone and reduce the preparative yields of CÀH-insertion products. Hence this photochemicalr eaction of diazoketones can be used for CÀHf unctionalization of different aliphatic compounds.Scheme1.Photochemical insertion of the terminalNatom of a4 -diazodihydrofuran-3(2H)-onei nto an a-CÀHb ondofT HF.

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A New Method for C−H Functionalization of Aliphatic Compounds by an Unusual Photochemical Reaction of Diazoketones without Elimination of Nitrogen

Rodina

Galkina

Maas

et al. 2016

Asian J Org Chem

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ChemInform Abstract: Eco‐Friendly Approach to Tetrasubstituted Diazodihydrofuranones: Valuable Precursors of Oxetane Derivatives and Other Heterocyclic Compounds.

et al. 2015

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Eco-Friendly Approach to Tetrasubstituted Diazodihydrofuranones: Valuable Precursors of Oxetane Derivatives and Other HeterocyclicCompounds. -The developed reaction sequence provides 2,2,5,5-tetraalkyl, 2,2,5,5-tetraaryl as well as regioisomeric 2,2-diaryl-5,5-dimethyl and 2,2-dimethyl-5,5-diaryldiazofuranones. -(GALKINA, O. S.; MAAS, G.; RODINA, L. L.; NIKOLAEV, V. A.; Synthesis 47 (2015) 10, 1469-1478, http://dx.

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Light-Induced Reactions of Diazotetrahydrofuranone without Elimination of Nitrogen: Experimental and Mechanistic Study

et al. 2017

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The energies and lifetimes of the excited states (S, S, S, T) of a diazotetrahydrofuranone were determined using experimental and computational methods. It was shown that direction of the diazoketone photochemical transformations without elimination of nitrogen is determined by multiplicity and energy of the excited state, generated by UV irradiation of diazo compound: isomerization to α-ketodiazirine proceeds from the singlet S state, whereas the alternative process of C-H insertion with hydrazone formation occurs through the triplet T state. The most probable excited state that leads to elimination of nitrogen and Wolff rearrangement is one of the highest singlet excited states of diazotetrahydrofuranone.

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Eco-Friendly Approach to Tetrasubstituted Diazodihydrofuranones: Valuable Precursors of Oxetane Derivatives and Other Heterocyclic Compounds

Abstract: Eco-friendly routes to 2,2,5,5-tetrasubstituted 4-diazodihydrofuran-3(2H)-ones were developed. In this manner, useful precursors to oxetane derivatives, potential NSAIDs, and other biologically active pharmaceuticals can be prepared without use of toxic reagents and solvents.

Cited by 3 publications

References 5 publications

A New Method for C−H Functionalization of Aliphatic Compounds by an Unusual Photochemical Reaction of Diazoketones without Elimination of Nitrogen

A New Method for C−H Functionalization of Aliphatic Compounds by an Unusual Photochemical Reaction of Diazoketones without Elimination of Nitrogen

ChemInform Abstract: Eco‐Friendly Approach to Tetrasubstituted Diazodihydrofuranones: Valuable Precursors of Oxetane Derivatives and Other Heterocyclic Compounds.

Light-Induced Reactions of Diazotetrahydrofuranone without Elimination of Nitrogen: Experimental and Mechanistic Study

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Eco-Friendly Approach to Tetrasubstituted Diazodihydrofuran­ones: Valuable Precursors of Oxetane Derivatives and Other Heterocyclic Compounds

Abstract: Eco-friendly routes to 2,2,5,5-tetrasubstituted 4-diazodihydrofuran-3(2H)-ones were developed. In this manner, useful precursors to oxetane derivatives, potential NSAIDs, and other biologically active pharmaceuticals can be prepared without use of toxic reagents and solvents.

Cited by 3 publications

References 5 publications

A New Method for C−H Functionalization of Aliphatic Compounds by an Unusual Photochemical Reaction of Diazoketones without Elimination of Nitrogen

A New Method for C−H Functionalization of Aliphatic Compounds by an Unusual Photochemical Reaction of Diazoketones without Elimination of Nitrogen

ChemInform Abstract: Eco‐Friendly Approach to Tetrasubstituted Diazodihydrofuranones: Valuable Precursors of Oxetane Derivatives and Other Heterocyclic Compounds.

Light-Induced Reactions of Diazotetrahydrofuranone without Elimination of Nitrogen: Experimental and Mechanistic Study

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Eco-Friendly Approach to Tetrasubstituted Diazodihydrofuranones: Valuable Precursors of Oxetane Derivatives and Other Heterocyclic Compounds