On Acylhydrazones and 1,2,3-Thiadiazoles

Hurd, Charles D.; Mori, Raymond I.

doi:10.1021/ja01625a047

Cited by 204 publications

(80 citation statements)

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“…Aus den Lösungen lassen sich die monosubstituierten Pentacarbonyl-Komplexe (7)(8)(9)(10)(11)(12) in guten Ausbeuten isolieren. Zu identischen Verbindungen kommt man auch, wenn man zunächst photochemisch erzeugtes (THF)M(CO)s mit äquivalenten Mengen Thiadiazol umsetzt.…”

Section: Ergebnisse Und Diskussionunclassified

“…Die gelben (7,8) Beim Vergleich der 13 C-NMR-Spektren sind vor allem die chemischen Verschiebungen der Kohlenstoffatome C4 und C5 interessant. Die Einbeziehung des ^-Systems bei der Komplexierung sollte sich durch eine signifikante Hochfeldverschiebung ihrer 13 C-Resonanzen bemerkbar machen [27][28][29].…”

Section: Ergebnisse Und Diskussionunclassified

“…Neben Thiophen und Selenophen [1,2] selbst, existiert eine Vielzahl 5-gliedriger Heterocyclen, in denen ein oder zwei Kohlenstoffatome durch Stickstoffatome ersetzt sind. Von den 1.2.3-, 1.2.5-, 1.3.4-und 1.2.4-Diaza-Isomeren waren für uns zunächst die leicht zugänglichen 1.2.3-Thiadiazole [3][4][5][6][7][8][9] (1) und 1.2.3-Selenadiazole [8][9][10][11][12][13][14][15] (2) von Interesse.…”

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Synthese und Struktur von 1.2.3-Thiadiazol- und 1.2.3-Selenadiazol-Pentaearbonyl-Komplexen der Elemente Chrom und Wolfram / Synthesis and Structure of 1,2,3-Thiadiazol- and 1,2,3-Selenadiazol-Pentacarbonyl-Complexes of the Elements Chromium and Tungsten

Bätzel

Boese

1981

Zeitschrift Für Naturforschung B

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Abstract From the reactions of (THF)M(CO)5 (M = Cr, W) with 4-phenyl-1,2,3-thiadiazol, 4-methyl-5-carboxylic acid-1,2,3-thiadiazol, 4-methyl-5-carboxylic acid ethyl ester-1,2,3-thiadiazol and 4-methyl-1,2,3-selenadiazol, pentacarbonyl-complexes are obtained as air stable compounds. IR spectra of products of similar reactions with M = Mo provide some evidence of the formation of analogous complexes. The thiadiazol complexes are also accessible directly, by photochemical displacement of carbonmonoxid in THF from the parent carbonyl. The X-ray structures of pentacarbonyl-(4-phenyl-1,2,3-thiadiazol)-tungsten and pentacarbonyl-(4-methyl-1,2,3-selenadiazol)-chromium show the coordina-tion of the ligand to the pentacarbonyl-metal-fragment via the nitrogen in position 2.

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Section: Ergebnisse Und Diskussionunclassified

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Synthese und Struktur von 1.2.3-Thiadiazol- und 1.2.3-Selenadiazol-Pentaearbonyl-Komplexen der Elemente Chrom und Wolfram / Synthesis and Structure of 1,2,3-Thiadiazol- and 1,2,3-Selenadiazol-Pentacarbonyl-Complexes of the Elements Chromium and Tungsten

Bätzel

Boese

1981

Zeitschrift Für Naturforschung B

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“…To this end, hetero-cyclization of semicarbazone 12 (as [C-C-N-N] unit) [8] to the corresponding 1,2,3-thiadiazole 9 (83%) was readily accomplished with SOCl 2 ([S] unit) [22]. By analogy to the above achieved Hurd-Mori reaction, the treatment of 4 with SeO 2 [23] in refluxing AcOH also proceeded to furnish primarily the selenadiazole 10 in 48% yield.…”

Section: Dmentioning

confidence: 99%

A Structurally Diverse Heterocyclic Library by Decoration of Oxcarbazepine Scaffold

et al. 2013

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A library of new heterocyclic systems was synthesized starting from oxcarbazepine (OXC, Trileptal ® , 10-oxo-10,11-dihydro-5H-dibenzo[b,f]azepine-5-carboxamide). The key for these transformations is the α-enolizable ketone present on the [d]-side of our starting material OXC, thus, an in depth investigation of the literature to find heteroannulation reactions for substrates carrying an α-enolizable ketone gave us a boost to discover an excellent derivatization strategy and [3+2], [4+2] and [4+1] approaches were successfully developed. Almost always a pre-functionalization was needed, but also the direct one-pot heterocycle construction was also explored.

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“…In spite of the obvious attraction of Se and Sheterocycles, only a few preparative routes have been described. Lalezari et al [4][5][6] were the first to report the synthesis of a 1,2,3-selenadiazole ring by analogy with the 1,2,3-thiadiazole system, which had been prepared previously by Hurd and Mori [7]. We report herein the synthesis of new compounds containing 1,2,3-selenadiazole and 1,2,3-thiadiazole rings using the Lalezari et …”

mentioning

confidence: 98%

New 1,2,3-Selenadiazole and 1,2,3-Thiadiazole Derivatives

Al-Smadi

Ratrout

2004

Molecules

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New 1,2,3-thiadiazole and 1,2,3-selenadiazole derivatives, 14-23, were prepared from the ketones 1-5 via the corresponding semicarbazones or hydrazones 6-12. The Hurd-Mori and Lalezari methods were used, respectively, for the preparation of these 1,2,3-thiadiazole and 1,2,3-selenadiazole derivatives. The intermediate 13 was also trapped, separated and fully characterized. These derivatives are important for photocrosslinking processes and due to their potential biological activity.

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On Acylhydrazones and 1,2,3-Thiadiazoles

Cited by 204 publications

References 1 publication

Synthese und Struktur von 1.2.3-Thiadiazol- und 1.2.3-Selenadiazol-Pentaearbonyl-Komplexen der Elemente Chrom und Wolfram / Synthesis and Structure of 1,2,3-Thiadiazol- and 1,2,3-Selenadiazol-Pentacarbonyl-Complexes of the Elements Chromium and Tungsten

Synthese und Struktur von 1.2.3-Thiadiazol- und 1.2.3-Selenadiazol-Pentaearbonyl-Komplexen der Elemente Chrom und Wolfram / Synthesis and Structure of 1,2,3-Thiadiazol- and 1,2,3-Selenadiazol-Pentacarbonyl-Complexes of the Elements Chromium and Tungsten

A Structurally Diverse Heterocyclic Library by Decoration of Oxcarbazepine Scaffold

New 1,2,3-Selenadiazole and 1,2,3-Thiadiazole Derivatives

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