2,2,4‐Trisubstituted 2H‐1,3‐Oxazetes ‐ A New Type of Heterocycles ‐ A Reinvestigation

Abstract

The recently described reaction between lithium hydride and addition products of acyl isothiocyanates with amines, methanol, and methanethiol in DMF followed by alkylation with methyl iodide is shown not to generate a new class of heterocycles -2,2,4-trisubstituted 2H-3,3-oxazetes but to yield N-acyl isothioureas, N-acyl mono-, and -dithioisocarbamates, respectively. The structures are confirmed by IR, mass, 'H-NMR, and 13C-NMR spectra. 2,2,4-Trisubstituierte ZH-l,3-Oxazete -Ein neuer Typ von Heterocyclen -Eine KlarstellungEs wird gezeigt, dal3 die kiirzlich beschriebene Reaktion von Lithiumhydrid mit Additionsprodukten aus Acylisothiocyanaten und Aminen, Methanol, sowie Methanthiol in DMF und nachfolgende Methylierung nicht zu neuen Heterocyclenden 2,2,4-trisubstituierten 2H-1,3-Oxazetenfiihrt, sondern N-Acylisothioharnstoffe, N-Acylmono-und -dithioisocarbamate ergibt. Deren Strukturen werden durch IR-, Massen-, 'H-NMR-und l3C-NMR-Spektren bestatigt.Recently Kristian, Kurschy, and Dzurillal) reported the synthesis of 2,2,4-trisubstituted 2H-1,3-oxazetes 1 -a hitherto undescribed class of four-membered heterocycles from acyl isothiocyanates via N-acyl thioureas, 0-methyl thiocarbamates, and methyl dithiocarbamates, respectively (Scheme 1).

Preparation of a steroid-oxazole-1,2′-[1,3]oxazete] derivative: biological and theoretical evaluation of its interaction with a kinase protein (CK2)

“…Several oxazete derivatives have been synthetized using some reagents such as mesitonitrile oxide [41], α,α-bis-(alkylthio) oxime [42], acylisothiocyanate [43] and others. In this study, an azete derivative was prepared via intramolecular reaction by displazament of nitro group in mild conditions (Fig.…”

New chloroamide-steroid derivative with biological activity on a casein kinase 2 (CK2)

“…It is noteworthy that several epoxides have been prepared using different protocols; nevertheless, expensive reagents and special conditions are required; the most widely practiced methods employ some reagents such as Co(III) [45] and Cr(III) [46]. In this study, three epoxide derivatives (compounds 8, 9 and 10) were prepared by the reaction of 7 with aldehyde derivatives in mild conditions ( Figure 6).…”

Synthesis of two 7,8-dioxabicyclo[4.1.1]octan-3-yl)-steroid derivatives and evaluation of their inotropic activity in an animal model.

“…There are several studies which have shown that molecular orbitals and frontier electron density can be used to predict the most reactive position in some electron system on several types of reactions [30,31]. In this way, the values of highest occupied molecular orbital (HOMO), lowest unoccupied molecular orbital (LUMO) and their energy gap reflect the chemical activity of a molecule [32].…”