Journal ArticleDOI
Heterocyclic compounds from alloxan and amines. XI. Uramils, dialuric acids, and related compounds
JW Clark-Lewis,K Moody +1 more
TLDR
In this paper, a number of uramils and 5-aryldialuric acids from o-substituted anilines are described, and their precursors are described.Abstract:
Preparation of a number of uramils and 5-aryldialuric acids from o-substituted anilines is described. Methylation of the uramils gave dimethoxy-N-monomethyl pyrimidine derivatives accompanied by minor amounts of trimethoxy-pyrimidines, and the dialuric acids gave 1,3-dimethylpyrimidines or 5-methoxy-1,3-dimethylbarbituric acids (with an excess of diazomethane). Ring contraction of the 1,3-dimethyldialuric acids gave the isomeric 5-N-methylcarbamoyloxazolidine-2,4-diones. The dialuric acid from dimedone gave a trimethyl derivative (a methoxycyclohexenyl-1,3-dimethyldialuric acid). Anthranilic acid and alloxan in acetic acid gave a benzoxazonespirobarbituric acid, but in aqueous ethanol yielded a dialuric acid which was characterized by conversion into several derivatives. Infrared and N.M.R. data are recorded for the uramils, dialuric acids, and their derivatives.read more
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Book ChapterDOI
Heterocycles by Ring Closure of Ortho-Substituted t-Anilines (The t-Amino Effect)
Otto Meth-Cohn,H. Suschitzky +1 more
TL;DR: In this article, the authors discuss the cyclizations of ortho-substituted t-anilines with an ortho substituent and the t-nitrogen and show that these cyclizations can be rationalized by an imine bearing a good leaving group.
Journal ArticleDOI
Photochemie des (Iso) Alloxazins, III. Intramolekulare Photodealkylierung von 10-Alkylisoalloxazinen, eine Modellreaktion für den Riboflavin-Photoabbau
Monika Gladys,Wolfgang-R. Knappe +1 more
TL;DR: A number of 10-alkyl and 10-cycloalkyl-isoalloxazines have been synthesized as discussed by the authors, and the results are compared to the photodegradation of riboflavine.
Journal ArticleDOI
Activation and transfer of oxygen. XVI: spontaneous electron transfer in flavinium salt solutions. A new principle for the development of oxygen activation models
H.I.X. Mager,R. Addink +1 more
TL;DR: In this paper, the conditions for a 10, 10, 1O a -ring opened intermediates were determined and the results of the O 2 -balance were consistent with the conclusion that the lO,lO a-ring opening is coupled with or followed by an electron transfer from a peroxy radical to RFl-A + · giving a generation of O 2.
Journal ArticleDOI
On the chemistry of flavin-dependent oxygen activation III. synthesis of 1.10a-dihydroflavin and its 10.10-aring opened derivative as model chromophores for enzyme-bound intermediates
TL;DR: In this article, the reaction mechanisms of flavin-dependent oxygenase and luciferase are discussed in terms of chemical structure, and a model chromophores of 1.10-dihydroflavin and its 10.10a-ring opened derivative have been isolated.
Journal ArticleDOI
Alloxan-(o-amino-anil) as model chromophore for a 10,10a-ring opened intermediate in flavin-dependent dioxygen activation
TL;DR: The mechanism of flavin-mediated dioxygen activation may involve reversible opening of the flavin ring system, as proposed for aromatic hydroxylases and for bacterial luciferase, and spectral properties of chromophores II and IV have been long subject to speculation.