2591-86-8Relevant articles and documents
Reactions of diazomethylphosphonate: The first synthesis of a formylphosphonate hydrate
Hamilton, Robert,McKervey, M. Anthony,Rafferty, M. Denise,Walker, Brian J.
, p. 441 - 444 (1996)
Formylphosphonate hydrate has been synthesised by the oxidation of diazomethylphosphonate with dimethyldioxirane (DMD) and its reactions, including the formation of imines, oximes, and Wittig olefination products, have been investigated. Formylphosphonate also acts as an efficient, selective formylating agent of secondary amines. β-Ketophosphonic acids derived from a range of amino acids have been prepared by the tin (II) chloride-catalysed reaction of diazomethylphosphonate with amino aldehydes and in certain cases shown to be potent inhibitors of leucine aminopeptidase.
-
Ando,Watanabe
, p. 947,948 (1977)
-
Jardine, I.,McQuillin, F. J.
, (1972)
-
Berbalk et al.
, p. 1081,1083, 1084 (1976)
-
Synthesis of 3-Amino-4-iodothiophenes through Iodocyclization of 1-(1,3-Dithian-2-yl)propargylamines
Ismailoglu, Eda,Mert, Zeynep,Dinc, Mert,Kaya, Kerem,Yucel, Baris
, p. 4107 - 4124 (2021)
1-(1,3-Dithian-2-yl)propargylamines undergo iodo-cylization regioselectively to afford tetrasubstituted 3-amino-4-iodothiophenes in 30–87 % yields by iodide induced cleavage of dithiane ring in a bicyclic sulfonium intermediate. A mechanism for this unprecedented transformation was proposed and tentatively supported by the isolation of an intermediate structure. 1-(1,3-Dithian-2-yl)propargylamines were prepared in 30–94 % yields by Au-catalyzed one-pot, three-component reaction of 1,3-dithiane-2-carbaldehydes, amines, and alkynes so called A3-coupling reaction.
-
Nefedov et al.
, (1973)
-
Dioxetane Formation at a Double Bond Adjacent to Bridgehead Nitrogen: Rapid Reaction between Neostrychnine and Singlet Oxygen in a Polar Protic Medium. Evidence Against the Intermediacy of an Open Zwitterion
Curtis, N. M.,Gorman, A. A.,Prescott, A. L.
, p. 7549 - 7550 (1988)
-
-
Rozhdestenskaya et al.
, (1977)
-
Chromium-catalysed efficient: N -formylation of amines with a recyclable polyoxometalate-supported green catalyst
Dan, Demin,Chen, Fubo,Zhao, Whenshu,Yu, Han,Han, Sheng,Wei, Yongge
supporting information, p. 90 - 94 (2021/01/11)
A simple and efficient protocol for the formylation of amines with formic acid, catalyzed by a polyoxometalate-based chromium catalyst, is described. Notably, this method shows excellent activity and chemoselectivity for the formylation of primary amines; diamines have also been successfully employed. Importantly, the chromium catalyst is potentially non-toxic, environmentally benign and safer than the widely used high valence chromium catalysts such as CrO3 and K2Cr2O7. The catalyst can be recycled several times with a negligible impact on activity. Finally, a plausible mechanism is provided based on the observation of intermediate and control experiments.
Amide Bond Formation via Aerobic Photooxidative Coupling of Aldehydes with Amines Catalyzed by a Riboflavin Derivative
Hassan Tolba, Amal,Krupi?ka, Martin,Chudoba, Josef,Cibulka, Radek
supporting information, p. 6825 - 6830 (2021/09/11)
We report an effective, operationally simple, and environmentally friendly system for the synthesis of tertiary amides by the oxidative coupling of aromatic or aliphatic aldehydes with amines mediated by riboflavin tetraacetate (RFTA), an inexpensive organic photocatalyst, and visible light using oxygen as the sole oxidant. The method is based on the oxidative power of an excited flavin catalyst and the relatively low oxidation potential of the hemiaminal formed by amine to aldehyde addition.
