Preparation of ethyl diazoacetate via a triazene intermediate

Baumgarten, Ronald J.

doi:10.1021/jo01288a059

Cited by 28 publications

(16 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…Common methods include (i) diazo transfer, 58,59 (ii) diazotization, 60,61 (iii) hydrazone decomposition 62,63 or hydrazone oxidation, 64,65 (iv) rearrangement of N -alkyl N -nitroso compounds, 8,66 (v) 1,3-disubstituted acyl (or aryl) triazine fragmentation, 67,68 and (vi) elaboration of other diazo compounds (Figure 2). 69–73 Most of these routes have been reviewed extensively for their merits in the context of synthetic chemistry.…”

Section: Preparationmentioning

confidence: 99%

See 1 more Smart Citation

Diazo Compounds: Versatile Tools for Chemical Biology

2016

View full text Add to dashboard Cite

Diazo groups have broad and tunable reactivity. That and other attributes endow diazo compounds with the potential to be valuable reagents for chemical biologists. The presence of diazo groups in natural products underscores their metabolic stability and anticipates their utility in a biological context. The chemoselectivity of diazo groups, even in the presence of azido groups, presents many opportunities. Already, diazo compounds have served as chemical probes and elicited novel modifications of proteins and nucleic acids. Here, we review advances that have facilitated the chemical synthesis of diazo compounds, and we highlight applications of diazo compounds in the detection and modification of biomolecules.

show abstract

Section: Preparationmentioning

confidence: 99%

“…The ensuing triazenophosphonium intermediate hydrolyzes quickly in water to form an acyl triazene, which is a known precursor to a diazo group. 67,68 …”

Section: Preparationmentioning

confidence: 99%

Diazo Compounds: Versatile Tools for Chemical Biology

2016

View full text Add to dashboard Cite

show abstract

“…Die Methode eignet sich auch, um a-Bromketone in a-Diazoketone umzuwandeln, wie am Beispiel von 2-Diazo-1-phenyl-1-ethanon (w-Diazoacetophenon) gezeigt wurde. [42] oder einer Base [43] die Fragmentierung zu einem a-Diazocarbonsäureester und einem aromatischen Amin ein (Schema 9). Wegen der begrenzten Anwendungsbreite und der mäßigen Ausbeuten hat diese Methode allerdings bisher keine präpa-rative Bedeutung erlangt.…”

Section: Diazoverbindungen Aus Hydrazonenunclassified

“…[38] Ist beim Oxidationsschritt auch eine [39] und 10 [40] (Schema 8) eingesetzt. Fukuyama und Mitarbeiter [41] haben kürzlich eine neue Diazoacetylierungsmethode vorgestellt, bei der aus a-Bromessigestern und N,N'-Ditosylhydrazin (11) [42] oder einer Base [43] die Fragmentierung zu einem a-Diazocarbonsäureester und einem aromatischen Amin ein (Schema 9). Wegen der begrenzten Anwendungsbreite und der mäßigen Ausbeuten hat diese Methode allerdings bisher keine präparative Bedeutung erlangt.…”

Section: Diazoverbindungen Aus Hydrazonenunclassified

Neues zur Synthese von Diazoverbindungen

Maas

2009

Angewandte Chemie

View full text Add to dashboard Cite

Aufgrund der vielseitigen und nützlichen Folgechemie von Diazoverbindungen (R1R2CN2) ist das Interesse an dieser Substanzklasse seit Jahren ungebrochen. Dabei wird auch das bereits vorhandene Methodenrepertoire zur Herstellung von Diazoverbindungen immer wieder um neue Verfahren oder um neuartige Varianten etablierter Synthesewege ergänzt. Nicht selten tragen die neuen Synthesevorschläge der Labilität und beachtlichen chemischen Reaktivität bestimmter Typen von Diazoverbindungen Rechnung, aber auch dem Aspekt umweltfreundlicherer Methodik wurde Beachtung geschenkt.

show abstract

“…Conversion of N-(p-nitrophenylazo)-glycine ethyl ester ( 3 0 ) to p-nitroaniline and ethyl diazoacetate proceeds smoothly in a two-phase system of niethylene chloride and 6% aqueous acetic acid (7). The diazoacetate can be formed quantitatively, without isolation of the intermediate triazene ( 3 a ) , by coupling the p-nitrobenzenediazonium salt and ethyl glycinate in dry dimethylformamide with a slight molar excess of triethylalnine (8).…”

Section: -Ethoxy-ih-l23-triazoles By Coupling Of Alkenediazoniummentioning

confidence: 99%

Open-chain nitrogen compounds. Part IV. Synthesis of 5-hydroxy-1,2,3-triazoles from 1-aryl-3-(ethoxycarbonylmethyl)triazenes: a new route to α-diazo-N-arylacetamides

Baines¹,

Vaughan²,

Hooper³

et al. 1983

Can. J. Chem.

View full text Add to dashboard Cite

. LEVECK. Can. J . Chcm. 61, 1549 (1983).A scries of triazcncs of typc ArN=N-NH-CH2C02Et.N-arylazoglycinc cthyl cstcrs. have becn prcpalrd by coupling the arcne diazonium salt, ArNZi.X , with cthyl glycinatc, NHZCH2C02Et; an clcctron-withdrawing substitucnt, c.g. NOZ, CN. C 0 2 R , and CI. in thc ortho or partr position of thc aryl group is csscntial for efficient coupling. Thc p-substituted arylazoglycinc cthyl cstcrs cyclizc when trcated with alcoholic potassium hyclroxidc to afford thc potassium salts of thc I-aryl-5-hydroxy-1.2.3-triazoles, which can bc obtained frcc by acidification of thc potassium salt solution with acctic acid. Rcaction of thc potassium salts with acctic anhydride yiclcls thc I-aryl-5-acetoxy-1.2.3-triazolcs. The 5-hydroxytriazolcs, whcn heatcd in ethanol, rcarrangc to a-diazoacctanilitlcs. ArNH .COCHN2. Thc diazoamidcs can be obtaincd in low yicld dircctly from thc triazcnes by prolonged rctluxing in cthanol. o-Substituted aryltriazcncs do not cyclizc undcr the samc conditions but fragmcnt to the arylaminc.

show abstract

Preparation of ethyl diazoacetate via a triazene intermediate

Cited by 28 publications

References 0 publications

Diazo Compounds: Versatile Tools for Chemical Biology

Diazo Compounds: Versatile Tools for Chemical Biology

Neues zur Synthese von Diazoverbindungen

Open-chain nitrogen compounds. Part IV. Synthesis of 5-hydroxy-1,2,3-triazoles from 1-aryl-3-(ethoxycarbonylmethyl)triazenes: a new route to α-diazo-N-arylacetamides

Contact Info

Product

Resources

About