Traditional and New methods for the Preparation of Diazocarbonyl Compounds

Burtoloso, Antonio C. B.; Momo, Patrícia B.; Novais, Graziele L.

doi:10.1590/0001-3765201820170768

Cited by 22 publications

(15 citation statements)

References 189 publications

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“…This result supports the extensive evidence reported by Regitz, Taber and others that the debenzoylation pathway is only observed when the α-carbon possesses an alkyl substituent. 64 , 65 , 89 − 92 …”

Section: Resultsmentioning

confidence: 99%

Exploiting Continuous Processing for Challenging Diazo Transfer and Telescoped Copper-Catalyzed Asymmetric Transformations

et al. 2021

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Generation and use of triflyl azide in flow enables efficient synthesis of a range of α-diazocarbonyl compounds, including α-diazoketones, α-diazoamides, and an α-diazosulfonyl ester, via both Regitz-type diazo transfer and deacylative/debenzoylative diazo-transfer processes with excellent yields and offers versatility in the solvent employed, in addition to addressing the hazards associated with handling of this highly reactive sulfonyl azide. Telescoping the generation of triflyl azide and diazo-transfer process with highly enantioselective copper-mediated intramolecular aromatic addition and C–H insertion processes demonstrates that the reaction stream containing the α-diazocarbonyl compound can be obtained in sufficient purity to pass directly over the immobilized copper bis(oxazoline) catalyst without detrimentally impacting the catalyst enantioselectivity.

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Section: Resultsmentioning

confidence: 99%

Exploiting Continuous Processing for Challenging Diazo Transfer and Telescoped Copper-Catalyzed Asymmetric Transformations

et al. 2021

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“…However, several new improved variants of the diazotransfer method and also new methods of synthesis of diazo compounds have emerged to date. [15][16][17] The reactions of α-diazocarbonyls and diazoalkanes in conventional methods are carried out by heating or by using UV light in appropriate solvent under inert atmosphere. The most common reactions proceed through intrusion of nitrogen leading to the generation of carbenes.…”

Section: A Brief Overview Of Synthesis and Chemistry Of Diazo Compoundsmentioning

confidence: 99%

“… [14] The reaction was carried out by stirring the reaction mixture at 20–40 °C for 2.5 hours. However, several new improved variants of the diazo‐transfer method and also new methods of synthesis of diazo compounds have emerged to date [15–17] …”

Section: A Brief Overview Of Synthesis and Chemistry Of Diazo Compoundsmentioning

confidence: 99%

Synthesis and Chemistry of Diazo Compounds under Microwave Irradiation: A Review

Singh

2022

Asian J Org Chem

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Diazo compounds such as α-diazocarbonyls, diazoalkanes, and diazoarenes are well known compounds in organic chemistry. Their synthetic utility is of paramount importance. They are commonly used as precursors of reactive intermediates like ketenes and carbenoids. Their reactions have been traditionally carried out under thermal or photochemical conditions in inert atmosphere. The synthesis and chemistry of such compounds under microwave irradiation have seen steady growth. The present article critically reviews the application of microwave irradiation in synthesis and chemistry of diazoalkanes and α-diazocarbonyls. The microwave-assisted reactions via ketenes and carbenes with alcohols, thiols, phenols, amines, imines, alkenes, alkynes, and three-membered heterocyclic compounds, etc. are described. These reactions furnish synthetically useful building blocks and also biologically relevant heterocyclic compounds. Most reactions are accelerated by the use of microwave irradiation. There are also some reports revealing that the reactions did not occur by conventional heating but yielded products on irradiation with microwaves. The mechanisms of the reactions where necessary and synthetic and biological relevance of the products are highlighted.

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“…Despite the fact that numerous modern, scalable and greener methods to obtain diazo carbonyl compounds were described over the past few years (Maas, 2009; Burtoloso et al, 2018), the development of greener, metal free, cheap and easily available catalysts for the efficient synthesis of cyclic urethanes is still highly desirable. With these demands in mind, efforts have been made to use Brønsted acid catalyst as a potential substitute to perform the desired transformation.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of Oxazinanones: Intramolecular Cyclization of Amino Acid-Derived Diazoketones via Silica-Supported HClO4 Catalysis

et al. 2019

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A Brønsted acid catalyzed intramolecular cyclization of N-Cbz-protected diazoketones, derived from α-amino acids, is described. The reaction proceeds under metal-free conditions and is promoted by ecofriendly silica-supported HClO4 as the catalyst and methanol as the solvent. This transformation enables the short synthesis of various 1,3-oxazinane-2,5-diones under mild reaction conditions and in good yields (up to 90%). The set-up is very simple; by just mixing all reagents together with no work-up necessary before purification, this protocol takes a greener approach.

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Traditional and New methods for the Preparation of Diazocarbonyl Compounds

Cited by 22 publications

References 189 publications

Exploiting Continuous Processing for Challenging Diazo Transfer and Telescoped Copper-Catalyzed Asymmetric Transformations

Exploiting Continuous Processing for Challenging Diazo Transfer and Telescoped Copper-Catalyzed Asymmetric Transformations

Synthesis and Chemistry of Diazo Compounds under Microwave Irradiation: A Review

Synthesis of Oxazinanones: Intramolecular Cyclization of Amino Acid-Derived Diazoketones via Silica-Supported HClO4 Catalysis

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