5-Phenylindazole

Hager, O.; Foces-Foces, C.; Jagerovic, N.; Elguero, J.; Trofimenko, S.

doi:10.1107/s0108270196007068

Cited by 3 publications

(2 citation statements)

References 5 publications

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“…Trimers are found for 7-methoxyindazole 4, 3d for two polymorphic forms of 3-phenylindazole, 30 for 3phenyl-5-methylindazole 31 and for 3-methylcarboxyindazole. 32 The parent 1H-indazole, 33 5-phenylindazole 29 and 7methylindazole 14 crystallize as one-dimensional catemers (two-fold screw axes). Obviously the formation of dimers, including 6, is not due to any specific substitution pattern.…”

Section: Nmr Spectroscopymentioning

confidence: 99%

The structure of fluorinated indazoles: the effect of the replacement of a H by a F atom on the supramolecular structure of NH-indazoles

et al. 2007

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The structures of three NH-indazoles (3-methyl, 3-trifluoromethyl and 3-trifluoromethyl-4,5,6,7tetrafluoroindazoles) have been determined by X-ray crystallography. These three compounds, together with 3-methyl-4,5,6,7-tetrafluoroindazole, whose X-ray structure could not be determined, have been studied using multinuclear magnetic resonance spectroscopy, including solid-state CPMAS. They all are 1H-tautomers. In the crystal, 3-methyl-1H-indazole forms hydrogen bonded dimers, whereas 3-trifluoromethyl-1H-indazole and 3-trifluoromethyl-4,5,6,7tetrafluoro-1H-indazole crystallize as catemers. These catemers are chiral space group P3 2. They are the first examples of indazoles crystallizing in the form of helices of threefold screw axis. Attempts at rationalizing this behavior on the basis of supramolecular interactions (hydrogen bonds and aromatic interactions) and GIAO calculations are discussed. The present paper focuses on the four related 1H-indazoles 6-9 depicted in Scheme 2. Scheme 1 Indazoles and a 3-trifluoromethylpyrazole of biological relevance.

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Section: Nmr Spectroscopymentioning

confidence: 99%

The structure of fluorinated indazoles: the effect of the replacement of a H by a F atom on the supramolecular structure of NH-indazoles

et al. 2007

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“…5-Phenylindazole, 5-methylindazole, 3-methylindazole, 1 H- benz[ g ]indazole, 3-methyl-1 H -benz[ g ]indazole, [(MeCN) 2 Mo(CO) 2 (η 3 -CH 2 CMeCH 2 )], and [RhCl(COD)] 2 were prepared by literature methods. All other chemicals were of reagent grade and were used as received.…”

Section: Methodsmentioning

confidence: 99%

Hydrotris(indazolyl)borates: Homoscorpionates with Tunable Regiochemistry

et al. 1997

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A series of hydrotris(indazolyl)borates containing diverse substituents on the indazole ring and representing two types of regiochemistries have been synthesized. Indazoles with a 7-alkyl substituent or a 6,7-fused benzo ring formed ligands with boron bonded to the less hindered N-2 ()Tp 3Bo ), while those with alkyl or aryl substituents in any other position yielded ligands with boron bonded to the more hindered N-1 ()Tp 4Bo ), thus being the first example of homoscorpionates with 4,5-substituents. Octahedral homo-and heteroleptic complexes of Co, Fe, and Zn have been prepared and characterized, as well as complexes of the typesand [Rh(L)(CO) 2 ]. X-ray crystallography provided structures of the complexes [Rh(HB{3-methylindazol-1-yl} 3 )(COD)], 1 (space group P2 1 /n; a ) 11.766(2), b ) 16.189(2), c ) 15.149(2) Å; β ) 92.51(1)°; Z ) 4; R ) 0.0306 for 4318 independent reflections), [Co(HB{7-methylinazol-2-yl} 3 )(HB{3neopentylpyrazol-1-yl} 3 )], 2 (space group P1 h; a ) 13.368(4), b ) 13.652(4), c ) 16.203(9) Å; R ) 73.73(4), β) 71.26(3), γ ) 63.54(2)°; Z ) 2; R ) 0.0761 for 7721 independent reflections), and indazol-2-yl}borate)(hydrotris{3-neopentylpyrazol-1-yl}borate)]‚C 6 H 5 CN, 3 (space group P1 h; a ) 13.216(6), b ) 13.706(4), c ) 17.881(6) Å; R ) 73.79(2), β ) 86.71(3), γ ) 85.61(3)°; Z ) 2; R ) 0.1138 for 6698 independent reflections).

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Synthesis and Structural Characterization of 1- and 2-Substituted Indazoles: Ester and Carboxylic Acid Derivatives

et al. 2006

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A series of indazoles substituted at the N-1 and N-2 positions with estercontaining side chains -(CH 2 ) n CO 2 R of different lengths (n = 0-6, 9, 10) are described. Nucleophilic substitution reactions on halo esters (X(CH 2 ) n CO 2 R) by 1H-indazole in alkaline solution lead to mixtures of N-1 and N-2 isomers, in which the N-1 isomer predominates. Basic hydrolysis of the ester derivatives allowed the synthesis of the corresponding indazole carboxylic acids. All compounds were fully characterised by multinuclear NMR and IR spectroscopies, MS spectrometry and elemental analysis; the NMR spectroscopic data were used for structural assignment of the N-1 and N-2 isomers. The molecular structure of indazol-2-yl-acetic acid (5b) was determined by X-ray diffraction, which shows a supramolecular architecture involving O2-H...N1 intermolecular hydrogen bonds.

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5-Phenylindazole

Cited by 3 publications

References 5 publications

The structure of fluorinated indazoles: the effect of the replacement of a H by a F atom on the supramolecular structure of NH-indazoles

The structure of fluorinated indazoles: the effect of the replacement of a H by a F atom on the supramolecular structure of NH-indazoles

Hydrotris(indazolyl)borates: Homoscorpionates with Tunable Regiochemistry

Synthesis and Structural Characterization of 1- and 2-Substituted Indazoles: Ester and Carboxylic Acid Derivatives

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