Reaction of 1,4-di-(3-aminofurazan-4-oyl)piperazine 4 with dibromoisocyanurate (DBI) affords azo-furazan-annulated macrocyclic lactam 7; the X-ray structure of the macrocycle 7 is reported. The synthesis was started with 3-aminofurazan-4-carboxylic acid 1. A one-pot method for preparation of the amino acid was elaborated from commercially available cyanoacetic ester. Amides of the acid have been prepared via the esterification and subsequent amination.

The first general synthetic route has been developed for the convenient preparation of iodofurazans. The approach was accomplished by one-pot diazotization-iodation reaction of appropriate aminofurazans. A combination of sodium nitrite and iodine in organic solvent under anhydrous conditions as the reaction conditions allowed to solve problem in iodofurazans preparation. The investigation of the substituent influence on NMR data of the iodofurazans has been carried out. The X-ray crystal structure of the 3-amino-4-iodofurazan 1d is reported. (C) 2004 Wiley Periodicals, Inc.

A series of chromophoric azofurazan-containing macrocycles 6a-c and 7a-d were synthesized from bis(aminofurazanylic) ethers of 1,2-diols 4a-d by dibromoisocyanurate oxidation.. The macrocycle closure is a result of N=N bond formation. An ion-binding ability of these compounds was tested. The macrocycles were characterized by NMR, MS, IR, and UV spectroscopy. The X-ray crystal structures of the macrocycles 6a, 7c, and linear counterpart 12 are reported. (C) 2004 Wiley Periodicals, Inc.

Nonselective attacks at the carbon bonded to a nitro group and carbon bonded to the N(O) atom of the azoxy group were observed in the reactions of 4,4′-dinitroazoxyfurazan with bases and nucleophiles. A mechanism is presented to account for both of the pathways to products. A series of new difurazanyl ether derivatives was synthesized. © 2000 John Wiley & Sons, Inc. Heteroatom Chem 11:48–56, 2000

Furazans bearing one and two chlorine atoms can be easily prepared by nucleophilic displacement of a nitro group at a furazan ring upon treatment with the Vilsmeier reagent.

The search of the new low-melting high energetic materials, which match the performance of TNAZ and more available, is the barest necessity. The syntheses of several novel zero-hydrogen but nitrogen and oxygen rich high energetic heterocycles, such as bridged nitrofurazans, were undertaken to test the hypothesis that accumulate furazan ring in such molecule could effectively serve in construction of energetically interesting materials. Eight dinitro trifurazans were synthesized and tested. The series of compounds was prepared in three--five stages from the 3,4-diaminofurazan(10). Oxy bridge was formed by utilizing hydroxyfurazans as nucleophiles. Azo bridge was prepared by oxidizing coupling of amino groups with KMnO4 in acid medium. Transformation of azo bridge to azoxy one was accomplished by mixture of(NH4)2S2O8 and oleum. The set of trifurazans represents a new class of low-melting high energetic materials which are among the most potent CxHyNzOw-explosives known. The isomeric diazoxyfurazans,(28),(29), and(30), differ dramatically in their properties. Liquid diazoxy compound(28) has density of 1.8 g/cm3 and is reach a record figure for CxHyNzOw-oil known. Die Suche nach neuen niedrigschmelzenden energiereichen Materialien, welche die Leistung von TNAZ erreichen oder übertreffen, ist zwingende Notwendigkeit. Die Synthesen von verschiedenen neuartigen nichtwasserstoff-, aber stickstoff- und sauerstoffreichen energetischen Heterocyclen, z.B. Nitrofurazane als Brückenglieder, wurden durchgeführt zur Prüfung der Hypothese, daß akkumulierte Furazanringe in solchen Molekülen wirksam sein könnten für die Konstruktion von energetisch wichtigen Materialien. Acht Dinitrotrifurazane wurden synthetisiert und getestet. Die Verbindungen wurden dargestellt in drei bis fünf Stufen aus 3,4-Diaminofurazan(10). Oxybrücken wurden gebildet durch Verwendung des Hydroxyfurazans als nukleophile Komponente. Azobrücken wurden dargestellt durch oxidierende Kupplung von Aminogruppen mit KMnO4in saurem Medium. Die Umlagerung der Azobrücken in Azoxybrücken wurde erreicht mit einer Mischung aus Ammoniumpersulfat und Oleum. Diese Trifurazanreihe repräsentiert eine neuartige Klasse von niedrigschmelzenden Energiestoffen unter den bekannten wirksamsten CxHyNzOw-Explosivstoffen. Die isomeren Dioxyfurazane(28),(29),(30) unterscheiden sich grundlegend in ihren Eigenschaften. Die flüssige Diazoxyverbindung(28) hat eine Dichte von 1,8 g/cm3und stellt eine Rekordverbindung für ein CxHyNzOw-Ö1 dar. La recherche de nouvelles substances énergétiques à base point de fusion qui atteignent ou surpassent les performances de TNAZ est d'une absolue nécessité. Les synthèses de différents hétérocycles énergétiques nouveaux contenant peu d'hydrogène, mais beaucoup d'azote et d'oxygène, tels que le nitrofurazane comme éléments de pont ont été effectuées pour vérifier l'hypothèse selon laquelle les anneaux accumulés de furazane dans de telles molécules pourraient être efficaces pour la formulation de substances énergétiquement importantes. Huit dinitrofurazanes ont été synthétisés et testés. Les combinaisons ont été représentées dans trois à cinq étages de 3,4-diaminofurazane(10). Des ponts oxydants ont été formés en utilisant l'hydroxyfurazane comme composant nucléophile. Des ponts azo ont été fabriqués par couplage oxydant de groupes amino avec KMnO4 en milieu acide. La transformation des ponts azo en ponts azozy a été obtenue pour un mélange de persulfate d'ammonium et d'oléum. Cette série trifurazane représente une classe nouvelle de substances énergétiques à bas point de fusion parmi les explosifs les plus efficaces CxHyNzOw bien connus. Les dioxyfurazanes isomères(28),(29),(30) se distinguent fondamentalement dans leurs propriétés. Le composé diazoxy(28) a une densité de 1,8 g/cm3 et constitue un composé record pour une huile CxHyNzOw.

The conformer populations for trans- and cis-2,3-disubstituted 1,4-dithianes have been determined by 1H and 13C NMR spectroscopy and calculated by molecular mechanics (MMX). The CH2X-substituents demonstrate the strong preference for axial position. The remarkable difference originating from intramolecular steric interactions has been observed between two trans-dialkyl derivatives: the trans-2,3-dimethyl-1,4-dithiane is predominantly equatorial whereas trans-2,3-dipropyl-1,4-dithiane prefers diaxial conformation. The properties of cis-2,3-dipropyl-1,4-dithiane are also unusual: its ring interconversion is unexpectedly slow (ΔG≠ = 11.2 kcal mol−1 at 26OK).