Synthesis and structural investigations of N(1-methyl-2-carbomethoxyindolyl-3-sulfonyl)-N?-hetarylureas

Сорокин, В. И.; Golosov, S. N.; Kornilov, A. N.; Klyuev, N. A.; Gorozhankin, S. K.; Yufit, D. S.; Struchkov, Yu. T.; Drozd, V. N.

doi:10.1007/bf01165698

Cited by 2 publications

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“…1. Bond lengths and angles in the molecule exhibit normal values (Allen et al, 1987) and are in good agreement with the few related crystal structures, which have been determined so far with comparable accuracy [refcodes RACCOO , XUYTUG , NAFWAT (Wang et al, 2004) and YUZHUW (Sorokin et al, 1993); Cambridge Structural Database, Version 5.31, with Aug. 2010 updates; Allen, 2002]. The molecule of the title compound can be divided into three approximately planar parts: (i) the triazinylsulfonylurea group including the triazine substituents N(CH 3 ) 2 and OCH 2 CF 3 comprising the 18 atoms S1, O2, O5, O6, N1 to N6, and C10 to C17 with a r.m.s.…”

Section: Methodssupporting

confidence: 86%

“…For the inhibition mechanism of sulfonylurea herbicides on acetohydroxy acid syntheases, see: Duggleby et al (2008); McCourt et al (2005). For the crystal structures of related sulfonylurea compounds, see: ; ; Wang et al (2004); Sorokin et al (1993); Liu et al (2008). For a description of the Cambridge Structural Database, see: Allen (2002).…”

Section: Related Literaturementioning

confidence: 99%

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The herbicide triflusulfuron-methyl

Mereiter

2011

Acta Cryst E

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The molecule of the title compound [systematic name: methyl 2-({[4-dimethylamino-6-(2,2,2-trifluoroethoxy)-1,3,5-triazin-2-yl]carbamoyl}sulfamoyl)-3-methylbenzoate], C17H19F3N6O6S, features a nearly planar (r.m.s. deviation = 0.098 Å) dimethylaminotriazinyl-urea group with a short intramolecular N—H⋯N hydrogen bond to a triazine N atom. An intramolecular dipole–dipole interaction between the sulfamide and carboxylate groups, with Os⋯Cc = 2.800 (1) Å and Ns⋯Oc = 2.835 (1) Å, controls the orientation of the methylbenzoate group and the shape of the molecule. The crystal structure is stabilized by intermolecular N—H⋯N hydrogen bonding, C—H⋯X (X = N,O) interactions and arene π–π stacking.

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Section: Methodssupporting

confidence: 86%

Section: Related Literaturementioning

confidence: 99%

The herbicide triflusulfuron-methyl

Mereiter

2011

Acta Cryst E

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Reaction cascades initiated by nucleophilic attack of heteropentalene mesomeric betaine and nitrogen-rich mesoionic tetrazolium-5-amides on electron-deficient unsaturated compounds. Synthesis of novel heterocyclic systemsElectronic supplementary information (ESI) available: synthesis of 4b; reactions of 11 and 17 with electron-deficient unsaturated compounds; alternative synthesis of 19 from 20. See http://www.rsc.org/suppdata/ob/b2/b211000h/

et al. 2003

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The reactions of heteropentalene mesomeric betaine 1 and nitrogen-rich mesoionic tetrazolium-5-amides 4, 11 and 16-18 with electron-deficient unsaturated compounds have been studied. Novel heterocyclic systems, tetrazolo[4,5-a][1,7]benzodiazonine inner salt 2 and 3-oxo-3,7-dihydro-2H-pyrazolo[3,4-b]pyridine 5, have been synthesized by the reactions of dimethyl acetylenedicarboxylate with 1 and tetrazolium-5-anilide 4, respectively, and fully characterized by X-ray crystallography. It has been found that the reactions of other tetrazolium-5-amides are also initiated by the nucleophilic addition of the electron-rich amide nitrogen to the electron-deficient unsaturated compounds.

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Synthesis and structural investigations of N(1-methyl-2-carbomethoxyindolyl-3-sulfonyl)-N?-hetarylureas

Cited by 2 publications

References 3 publications

The herbicide triflusulfuron-methyl

The herbicide triflusulfuron-methyl

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