The crystal and molecular structure of 2-methyl-5-[methyl(mesyl)amino]-2<i>H</i>-1,2,3-triazole-4-carbonitrile. On the geometry of the <i>N</i>-mesyl groups

Kàlmán, Alajos; Parkanyi, L.; Schawartz, J.

doi:10.1107/s0567740877010322

Acta Crystallogr Sect B

1977

DOI: 10.1107/s0567740877010322

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The crystal and molecular structure of 2-methyl-5-[methyl(mesyl)amino]-2H-1,2,3-triazole-4-carbonitrile. On the geometry of the N-mesyl groups

Alajos Kàlmán¹,

L. Parkanyi²,

J. Schawartz³

Abstract: C6H9NsO2S is orthorhombic, space group Pbca, with a = 7.333 (4), b = 16.040 (2), c = 16.825 (3) A, Z = 8. The structure was refined to R = 0.073 for 1030 observed reflexions. The endocyclic methyl group is attached to N(2). The geometrical features of the N-mesyl groups as revealed in different crystal structures are discussed.

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1980

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Cited by 8 publications

References 14 publications

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Heterocyclic Rearrangement of 4,5,6,7‐Tetrahydro‐6,6‐dimethyl‐benzo[c][1,2,5]oxadiazol‐4‐one (Z)‐Arylhydrazones into Corresponding 2‐Aryl‐4,5,6,7‐tetrahydro‐2H‐benzo[d][1,2,3]triazol‐4‐one Oximes

Lefkopoulou¹,

Stephanidou‐Stephanatou²,

Tsoleridis³

et al. 1985

Helvetica Chimica Acta

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182. Heterocyclic Rearrangement of 4,5,6,7-Tetrahydro-6,6-dimethylbenzo[c] [ 1,2,5]oxadiazol-4-one (Z)-Arylhydrazones into Corresponding 2-Aryl-4,5,6,7-tetrahydro-2H-benzo[d] [ 1,2,3]triazo1-4-one Oximes The thermal base-catalysed and photochemical transformation (Boulton-Kutritzky rearrangement) of the title tetrahydrobenzo[c][l,2,5]oxadiazoles to tetrahydro-2H-benzo[d] [1,2,3]triazoles is studied. Attempts to induce analogous rearrangement in tetrahydro-2H-benzo[d] [ 1,2,3]triazol-4-one arylhydrazones or oximes failed. Some CND0/2 calculations are also carried out.We have reported previously [ 13 [2] that attempts to induce thermal or photochemical mononuclear heterocyclic rearrangement in 2-aryl-4,5,6,7-tetrahydro-6,6-dimethyl-2Hbenzo[d] [ 1,2,3]triazo1-4-one (Z)-arylhydrazones were unsuccessful. This prompted us to a more systematic study in order to examine whether this unsuccessful rearrangement [3] i Z; either due to the thermodynamical stability of the triazole ring [4] [5] or to an unfavored geometry of the condensed ring system.The present study is concerned with Boulton-Katritzky-type rearrangements [6] [7] of 4,5,6,7-tetrahydro-6,6-dimethylbenzo[c] [ 1,2,5]oxadiazo1-4-one (Z)-arylhydrazones (2) to the corresponding 2-aryl-4,5,6,7-tetrahydro-2H-benzo[d] [ 1,2,3]triazo1-4-one oximes (3). Comparatively few examples of ring transformations of 1,2,5-0xadiazoles to 1,2,3-Scheme I

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Heterocyclic Rearrangement of 4,5,6,7‐Tetrahydro‐6,6‐dimethyl‐benzo[c][1,2,5]oxadiazol‐4‐one (Z)‐Arylhydrazones into Corresponding 2‐Aryl‐4,5,6,7‐tetrahydro‐2H‐benzo[d][1,2,3]triazol‐4‐one Oximes

Lefkopoulou¹,

Stephanidou‐Stephanatou²,

Tsoleridis³

et al. 1985

Helvetica Chimica Acta

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Darstellung und Eigenschaften von 2,3‐disubstituierten 1,2‐Thiazetidin‐1, 1‐dioxiden

1985

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Aus Natrium-(2-phenylethensulfonat) (2) werden die 2-Alkylamino-2-phenylethansulfonsauren 3 hergestellt, aus denen nach Chlorierung durch RingschluR die Titelverbindungen 5 erhalten werden. Ihre Strukturen werden durch IR-und NMR-Spektren charakterisiert und mit denen analoger p-Lactame verglichen. Eine Rontgenstrukturanalyse von 5d bestatigt die vorgeschlagene Struktur.Synthesis and Structure of 2,3-Disubstituted 1,2-Thiazetidine 1,l-Dioxides 2-Alkylamino.2-phenylethanesulfonic acids 3 are prepared from sodium 2-phenylethenesulfonate (2). Compounds 3 are chlorinated and cyclized to yield the title compounds 5. Their structures are characterized by IR and NMR spectroscopy and compared to those of analogous p-lactams. An X-ray analysis of the P-sultam 5d establishes the proposed structure.Wahrend Darstellung und Reaktionsverhalten der hohergliedrigen Sultame bereits ausfuhrlich untersucht worden sind'-5), waren 1,2-Thiazetidin-l ,I-dioxide (B-Sultame) bisher wenig bekannt. In den letzen Jahren konnten zwar Synthesen fur einige speziell substituierte Beispiele vorgestellt werden6-'I), Verfahren fur die Herstellung wenig substituierter p-Sultame existierten jedoch bisher nicht. Vor kurzem beschrieben wir eine Synthese von N-substituiertenI2) und bicyclischen p-Sultamen'3). Hier sol1 uber die Darstellung von 2,3-disubstituierten b-Sultamen und uber einige ihrer Eigenschaften berichtet werden.Entsprechend der Darstellung N-substituierter p-Sultame konnen 2,3-disubstituierte 8-Sultame durch Cyclisierung substituierter 13-Aminosulfonsauren erhalten werden. Dazu wurde zunachst nach einer Vorschrift von Culbertson und Dietzt4) aus Styrol und Sulfurylchlorid das ungesattigte Sulfonsaurechlorid 1 gewonnen. Dies konnte durch Erhitzen mit waDriger Natriumhydroxidlosung bei 60°C in das Natriumsulfonat 2 ubergefuhrt werdenI5). 2 wurde sodann mit einem groBen Uberschuf3 waflriger

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Stereochemische Untersuchungen heterocyclischer Verbindungen. XII. Kristall‐ und Molekülstruktur von 1‐(2‐Amino‐1‐cyano‐2‐thio‐ethylen)pyridiniumyliden

et al. 1983

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Stereochemical Investigations of Heterocyclic Compounds. XII. Structural Investigations of 1‐(2‐Amino‐1‐cyano‐2‐thio)ethene Pyridinium Ylides Two isomerization processes were found by 1H‐d‐n. m. r. characterized by ΔG* = 67 ± 4 KJ/mol for E‐ Z‐isomerization and ΔG* = 46 ± 5 KJ/mol for the hindered rotation of the pyridine substituent in 1a. The structure of 1b was solved by direct method. Crystals are monoclinic space group P21/n, a = 13.682(3), b = 9.452(1), C = 19.713(6) Å, β = 96.42(2)°, V = 2533.3 Å3, Dx = 1.328 Mg · m−3, Z = 8. Both E‐ and Z‐isomeres of 2b are found in the crystal lattice. The aminoC distance with 1.369 (1,387) Å is shorter than the theoretical single bond distance. The formal CC double bond with 1.377 (1.391) Å is considerably longer than 1.337 Å observed in the some alkenes.

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The crystal and molecular structure of 2-methyl-5-[methyl(mesyl)amino]-2H-1,2,3-triazole-4-carbonitrile. On the geometry of the N-mesyl groups

Cited by 8 publications

References 14 publications

Heterocyclic Rearrangement of 4,5,6,7‐Tetrahydro‐6,6‐dimethyl‐benzo[c][1,2,5]oxadiazol‐4‐one (Z)‐Arylhydrazones into Corresponding 2‐Aryl‐4,5,6,7‐tetrahydro‐2H‐benzo[d][1,2,3]triazol‐4‐one Oximes

Heterocyclic Rearrangement of 4,5,6,7‐Tetrahydro‐6,6‐dimethyl‐benzo[c][1,2,5]oxadiazol‐4‐one (Z)‐Arylhydrazones into Corresponding 2‐Aryl‐4,5,6,7‐tetrahydro‐2H‐benzo[d][1,2,3]triazol‐4‐one Oximes

Darstellung und Eigenschaften von 2,3‐disubstituierten 1,2‐Thiazetidin‐1, 1‐dioxiden

Stereochemische Untersuchungen heterocyclischer Verbindungen. XII. Kristall‐ und Molekülstruktur von 1‐(2‐Amino‐1‐cyano‐2‐thio‐ethylen)pyridiniumyliden

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