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Roy, M.S.; Saxena, Dhiraj; Manmeeta,; Sharma, G. D.

doi:10.1023/a:1011220712873

Cited by 4 publications

(4 citation statements)

References 13 publications

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“…Compound 7 is of interest, because it is the precursor to 4,7‐dinitro‐4,5,6,7‐tetrahydro[1,2,5]oxadiazolo[3,4‐ b ]pyrazine, 11 , a well‐known energetic material [2]. It has also shown interesting electronic properties [9–11]. The original four‐step synthesis of 7 is shown in Scheme .…”

Section: Resultsmentioning

confidence: 99%

A Re‐Examination of the Reaction of 3,4‐Diamino[1,2,5]oxadiazole with Glyoxal

Willer

Storey

Campbell

et al. 2012

Journal of Heterocyclic Chem

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Reaction coordinate mapping was used to study the reaction of 3,4‐diamino[1,2,5]oxadiazole (3,4‐diaminofurazan) and 3,4‐diamino[1,2,5]thiadiazole with glyoxal. The thiadiazole was known to give a good yield of [1,2,5]thiadiazolo[3,4‐b]pyrazine, whereas the oxadiazole had not yielded, until now, [1,2,5]oxadiazolo[3,4‐b]pyrazine (or furazano[2,3‐b]pyrazine). The calculations suggested that the diols, 5,6‐dihydroxy‐4,5,6,7‐tetrahydro[1,2,5]oxadiazolo[3,4‐b]pyrazine and 5,6‐dihydroxy‐4,5,6,7‐tetrahydro[1,2,5]thiadiazolo[3,4‐b]pyrazine should be stable intermediates, and once formed, should provide a pathway to the target compounds via two dehydration steps, under forcing conditions. With this information in mind, the reactions of 3,4‐diamino[1,2,5]oxadiazole with glyoxal and pyruvic aldehyde were re‐examined. The reaction of 3,4‐diamino[1,2,5]oxadiazole with glyoxal and pyruvic aldehyde produced, under slightly basic conditions, a near quantitative yield of the expected initial products, 5,6‐dihydroxy‐4,5,6,7‐tetrahydro[1,2,5]oxadiazolo[3,4‐b]pyrazine and the 5‐methyl analog, respectively. The diols were easily isolated by lyophilizing the aqueous reaction mixture. The diols were pyrolized on silica gel at 160°C to give the desired [1,2,5]oxadiazolo[3,4‐b]pyrazine and the 5‐methyl analog. Both compounds were easily reduced to the corresponding 4,5,6,7‐tetrahydro‐derivative using sodium borohydride in THF/methanol. The [1,2,5]oxadiazolo[3,4‐b]pyrazine also displayed other interesting chemistry.

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Section: Resultsmentioning

confidence: 99%

A Re‐Examination of the Reaction of 3,4‐Diamino[1,2,5]oxadiazole with Glyoxal

Willer

Storey

Campbell

et al. 2012

Journal of Heterocyclic Chem

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“…The ability to controllably enhance charge transport in organic semiconductors via doping has garnered a lot of scientific attention. − In diodes and photovoltaic devices, doping of organic semiconductors can significantly increase current densities. , Similar processes have been shown to dramatically improve carrier mobility in organic thin-film transistors . In inorganics, doping entails the introduction of electron donors and acceptors as dopants to generate loosely bound electrons and holes, respectively, for enhanced charge transport.…”

Section: Introductionmentioning

confidence: 99%

“…Viologen, of various salt forms, has been used as effective electron transfer catalysts and electron mediators during photosynthesis and photochemical studies. − From the standpoint of doping, viologen has been incorporated in fractional amounts in organic semiconductors of furazano(3,4-b)piperrazine, FP, and poly( p -phenylene vinylene), PPV, to improve hole transport. Both FP and PPV exhibit p-characteristics; incorporation of viologen abstracts electrons (V +• in Scheme ), thereby increasing hole transport in the host organic semiconductors.…”

Section: Introductionmentioning

confidence: 99%

Cobaltocene-Doped Viologen as Functional Components in Organic Electronics

et al. 2009

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Given the energy level alignment between viologen and cobaltocene, cobaltocene readily transfers electrons to the intrinsically insulating viologen, resulting in the formation of an electron transfer complex with high electron density. When cobaltocene-viologen is incorporated as active layers in organic thin-film transistors, the output current of devices scales with increasing cobaltocene concentrations. We further demonstrate that cobaltocene-viologen makes effective electron transport layers in inverted polymer solar cells.

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“…However, the degree of bond fixation in the heterodienic fragment of furazan is very high, and its derivatives are not susceptible to tautomerism. According to ref , the furazan ring constitutes a part of high energy materials, while the polynitrogenous derivatives of furazanopyrazine have been proposed for use as explosives. , Aforesaid studies have contributed to the development of methods for the synthesis of furazanopyrazines − and have stimulated investigations into their physical and biological , properties. Heterocycles containing an oxadiazole moiety possess antiatherogenic, antimalarial, and antimicrobial , activities, as well as neuroprotective and antiproliferative effects.…”

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confidence: 99%

First Example of Catalytic Synthesis of Difurazanohexahydrohexaazapyrenes and in Vitro Study of Their Antitumor Activity

Rakhimova

Kirsanov

Mescheryakova

et al. 2019

ACS Med. Chem. Lett.

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Catalytic method for synthesis of hexahydrohexaazapyrenes bearing two annelated furazan moieties has been successfully developed. Structures of synthesized hexahydrodioxadecaazadicyclopenta[e,l]pyrenes have been determined on the basis of NMR data using 2D techniques, MALDI TOF/ TOF mass spectrometry, and X-ray analysis. Primary screening of hexahydrodioxadecaazadicyclopenta[e,l]pyrenes for cytotoxic activity against the K562, Jurkat, U937, and HeLa tumor cell lines has been performed. Studies on the induction of apoptosis and the effect of the synthesized compounds on the cell cycle have been successfully implemented. The synthesized compounds have been found to induce apoptosis of cancer cells in the K562, Jurkat, U937, and HeLa lines.

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Cited by 4 publications

References 13 publications

A Re‐Examination of the Reaction of 3,4‐Diamino[1,2,5]oxadiazole with Glyoxal

A Re‐Examination of the Reaction of 3,4‐Diamino[1,2,5]oxadiazole with Glyoxal

Cobaltocene-Doped Viologen as Functional Components in Organic Electronics

First Example of Catalytic Synthesis of Difurazanohexahydrohexaazapyrenes and in Vitro Study of Their Antitumor Activity

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