The simplest all-nitrogen ring: Photolytically filling the cyclic-N3 well

Peter C. Samartzis; Jim Jr-Min Lin; Tao-Tsung Ching; Chanchal Chaudhuri; Shih-Huang Lee; Alec M. Wodtke

doi:10.1063/1.2433723

Antimonial analogues of the acridine series. Dilhydrostibacridines

Proceedings of the Royal Society of London. Series A, Containing Papers of a Mathematical and Physical Character ◽

10.1098/rspa.1933.0201 ◽

1933 ◽

Vol 143 (848) ◽

pp. 38-47 ◽

Cited By ~ 8

Keyword(s):

Nitro Derivative ◽

Starting Material ◽

Arsenic Compounds ◽

Ring Systems ◽

Nitrogen Ring ◽

Derivatives Of

In pursuing our investigation out the antimony analogues of certain nitrogen ring-systems, we Lave now succeeded in obtaining derivatives of dilhydrostibacridines, of when some of the corresponding arsenic compounds have been studied recently by Gump and Stolzenburg. The starting material for the work was o -aminodiphenylmethane obtained from the corresponding nitro derivative when, in turn, was prepared from o -nitrobenzyl chloride and benzene by Taneseseu's modification of the Friedel-Crafts reaction.

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Synthese und Kristallstruktur des 2.4-Di-terf-butoxy-2,4-di-terfbutylcyclodisilazans / Synthesis and Crystal Structure of 2.4-Di-terf-butoxy-2,4-di-terrbutylcyclodisilazane

Zeitschrift für Naturforschung B ◽

10.1515/znb-1995-0526 ◽

1995 ◽

Vol 50 (5) ◽

pp. 844-847 ◽

Cited By ~ 5

Author(s):

Sven Dielkus ◽

Dorothee Großkopf ◽

Regine Herbst-Irmer ◽

Uwe Klingebiel

Keyword(s):

Crystal Structure ◽

Molar Ratio ◽

Synthesis And Crystal Structure ◽

Lithium Derivative ◽

Nitrogen Ring

Abstract Me3CSiHal3 react with LiOCMe3 to give Me3CO(Me3C)SiHal2 (HaI = F (1), Cl (3)). The aminofluorosilane, Me3CO(Me3C)SiFNH2 (2), is formed in the reaction of 1 with LiNH2. The diaminosilane Me3CO(Me3C)Si(NH2)2 (4) is obtained from the reaction of 2 with ammonia. 4 reacts with LiC4H9 to give the lithium derivative Me3CO(Me3C)Si(NHLi)NH2 (5). In a molar ratio 1:1 the reaction of 5 and 1 leads to the formation of the 1-amino-3-fluoro-disilazane Me3CO(Me3C)SiF- NH - SiNH2(CMe3)OCMe3 (6) and in a molar ratio 2:1 to the four-membered silicon nitrogen ring [Me3CO(M e3C)Si-NH]2 (7). The crystal structure of 7 was determined.

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Codeine analogs. Synthesis of 4a-aryldecahydroisoquinolines containing nitrogen ring functionality and of octahydro-1H-indeno[1,2,3-ef]isoquinolines. A total synthesis of codeine

The Journal of Organic Chemistry ◽

10.1021/jo00150a017 ◽

1983 ◽

Vol 48 (2) ◽

pp. 227-238 ◽

Cited By ~ 43

Author(s):

Walter H. Moos ◽

Richard D. Gless ◽

Henry Rapoport

Keyword(s):

Total Synthesis ◽

Nitrogen Ring

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The binding of analogues of coralyne and related heterocyclics to DNA triplexes

Biochemistry and Cell Biology ◽

10.1139/o95-002 ◽

1995 ◽

Vol 73 (1-2) ◽

pp. 11-18 ◽

Cited By ~ 25

Author(s):

Laura J. P. Latimer ◽

Natasha Payton ◽

Gavin Forsyth ◽

Jeremy S. Lee

Keyword(s):

Thermal Denaturation ◽

Positive Charge ◽

Triplex Dna ◽

Alkyl Chains ◽

Dna Triplexes ◽

Weak Binding ◽

Related Alkaloid ◽

General Preference ◽

Nitrogen Ring ◽

Derivatives Of

Coralyne has been shown previously to bind well to both T∙A∙T- and C∙G∙C+-containing triplexes. Derivatives of coralyne were prepared and their binding to poly(dT)∙poly(dA)∙poly(dT) and poly[d(TC)]∙poly[d(GA)]∙poly[d(C+T)] was assessed from thermal denaturation profiles. A tetraethoxy derivative showed only weak binding to both types of triplex. Analogues with extended 8-alkyl chains showed good binding to poly(dT)∙poly(dA)∙poly(dT), but the preference for triplex poly[d(TC)]∙poly[d(GA)]∙poly[d(C+T)] was decreased compared with the duplex. Sanguinarine, a related alkaloid, bound well to poly(dT)∙poly(dA)∙poly(dT) but only weakly to the protonated triplex. It is hypothesized that the position of the protonated nitrogen ring is important for binding to poly[d(TC)]∙poly[d(GA)]∙poly[d(C+T)]. A series of other chromophores was studied and only those with a positive charge bound to triplexes. All of these bound well to poly(dT)∙poly(dA)∙poly(dT) but only weakly if at all to the duplex poly(dA)∙poly(dT). In contrast, most of them did not bind well to the triplex poly[d(TC)]∙poly[d(GA)]∙poly[d(C+T)] and those that did still showed a preference for duplex poly[d(TC)]∙poly[d(GA)]. In general, preference for triplex poly(dT)∙poly(dA)∙poly(dT) compared with the duplex is a common feature of intercalating drugs. On the other hand, specificity for protonated triplexes may be very difficult to achieve.Key words: triplex DNA, DNA-binding drugs, intercalation.

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Observation of Photochemical C−N Bond Cleavage in CH3N3: A New Photochemical Route to Cyclic N3

The Journal of Physical Chemistry A ◽

10.1021/jp076779h ◽

2008 ◽

Vol 112 (6) ◽

pp. 1105-1111 ◽

Cited By ~ 23

Author(s):

Christopher Larson ◽

Ji ◽

Peter C. Samartzis ◽

Alfredo Quinto-Hernandez ◽

Jim Jr-Min Lin ◽

...

Keyword(s):

Bond Cleavage ◽

Cyclic N3 ◽

Photochemical Route

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THE EPIMERIZATION OF DELCOSINE

Canadian Journal of Chemistry ◽

10.1139/v61-201 ◽

1961 ◽

Vol 39 (8) ◽

pp. 1579-1587 ◽

Cited By ~ 7

Author(s):

Vinko Skarić ◽

Léo Marion

Keyword(s):

Infrared Spectra ◽

Potassium Hydroxide ◽

Methoxyl Group ◽

Hydroxyl Group ◽

Sodium Amalgam ◽

Acid Catalyzed ◽

Nitrogen Ring

Delcosine has been assigned tentatively the same C—N skeleton as lycoctonine. In lycoctonine, ring A carries at C-1 a methoxyl group which is directed away from the nitrogen ring. In delcosine, C-1 carries a hydroxyl group which has the opposite configuration and is directed towards the nitrogen. An attempt to correlate the two structures first involves epimerization at C-1 in delcosine. This has been carried out by oxidation of desethyldelcosine to an azomethine, the ethiodide of which, by the action of methanolic potassium hydroxide, is converted to oxo-1-epidelcosine in two steps. Oxo-1-epidelcosine in an acid-catalyzed rearrangement is transformed to a pinacone which, after methylation, gives O,O-dimethyl-anhydro-oxo-1-epidelcosine. This compound was compared with O-methylanhydro-oxolycoctonine, prepared from oxolycoctonine, but was not identical. Removal of a methoxyl, which in each compound is ortho to a carbonyl, by the action of sodium amalgam, produced O,O-dimethyl-6-desmethoxy-anhydro-oxo-1-epidelcosine and O-methyl-6-desmethoxy-anhydro-oxolycoctonine, which are not identical, but show in their infrared spectra much less dissimilarity than the spectra of the pair of compounds from which they were derived. These results are discussed in terms of the structure of delcosine.

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