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)
-
DMF·HCl as a versatile and straightforward N- and O-formylating agent
Ramírez-Vázquez, Dulce G.,Vi?as-Bravo, Omar,Martínez-Pascual, Roxana,Pérez-Picaso, Lemuel,Castro-Cerritos, Karla Viridiana
supporting information, p. 585 - 592 (2020/11/19)
Inspired by the serendipitous isolation of N-formylpiperazines when we attempted the synthesis of a series of piperazines, we have developed a straightforward methodology for the N- and O- formylation of secondary cyclic amines, anilines and steroids, respectively. Such approach is based on the hitherto non-reported use of DMF·HCl complex, as a versatile and easily-available formylating system that can be stored without apparent loss of activity.
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.