Crystal structure of indole derivatives

Голубев, С. С.; Kondrashev, Yu. D.

doi:10.1007/bf00749344

Cited by 3 publications

(3 citation statements)

References 4 publications

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“…The indole ring is conformationally rigid, but the dimethylamino part of the molecule has conformational variation as seen from the different torsion angles of crystallographically independent molecules in the crystal structure. In N,N-dimethyl-1H-indole-3-methanamine, 30 33 equivalent torsion angles were found to be similar, with values between 92.42°and 103.70°.…”

Section: Crystal Structuresmentioning

confidence: 91%

Synthesis and Structural Evaluation of 5-Methyl-6-acetyl Substituted Indole and Gramine

Kukuljan

Kranjc

Perdih

2016

ACSi

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The synthesis and crystal structures of 1-(5-methyl-1H-indol-6-yl)ethan-1-one (7), C 11 H 11 NO, and 1-{3-[(dimethylamino)methyl]-5-methyl-1H-indol-6-yl}ethan-1-one (8), C 14 H 18 N 2 O, are reported. The synthesis is based on the Diels-Alder cycloaddition of a substituted 2H-pyran-2-one derivative, followed by an acid-catalyzed cyclization and concomitant deprotection (the last two steps were carried out as a one-pot domino process) yielding substituted indole 7, which was further derivatized via Mannich reaction to the gramine derivative 8. Both structures 7 and 8 were determined on the basis of IR, 1 H NMR and mass spectroscopy, as well as by the elemental analysis and melting point determination. According to the single-crystal X-Ray diffraction analysis, the structure 7 has a single unique molecule in the asymmetric unit whereas the structure 8 contains four unique molecules in the asymmetric unit. Molecules 7 are linked via N-H···O hydrogen bonds between the secondary amine group and carbonyl moiety of the acetyl group of adjacent molecules, whereas molecules 8 are linked via N-H···N hydrogen bonds between the secondary and tertiary amine groups of adjacent molecules. Both structures are further stabilized by weak C-H···O, C-H···π and π···π interactions.

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Section: Crystal Structuresmentioning

confidence: 91%

Synthesis and Structural Evaluation of 5-Methyl-6-acetyl Substituted Indole and Gramine

Kukuljan

Kranjc

Perdih

2016

ACSi

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“…For a related structure, see: Golubev & Kondrashev (1984 Data collection: CrysAlis PRO (Agilent, 2010); cell refinement: CrysAlis PRO; data reduction: CrysAlis PRO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: ORTEPIII (Burnett & Johnson, 1996), ORTEP-3 for Windows (Farrugia, 1999) and PLATON (Spek, 2009); software used to prepare material for publication: SHELXL97. …”

Section: Related Literaturementioning

confidence: 99%

[(5-Bromo-1H-indol-3-yl)methyl]dimethylazanium nitrate

Wang

et al. 2011

Acta Cryst E

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“…On the other hand, the C 5 -C 6 bond (1.446 Å) is a typical single C sp 2-C sp 2 bond [16]. An analogous effect on the indole ring (i.e., bond lengths therein) is produced by the carbonyl group in position 3 of, e.g., 1H-indole-3-carbaldehyde, where the corresponding bond lengths are 1.389 and 1.382 Å, respectively [18]. Some specific features were also found in the indole fragment.…”

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confidence: 99%

Synthesis and Structure of 5-Indolyl-6-thienyl-1,2,4-triazines

et al. 2005

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Acylation of indole and 2,5-dimethylthiophene with 2-(3-indolyl)-2-oxoacetyl chloride afforded the corresponding diketones. 1-(2,5-Dimethyl-3-thienyl)-2-(3-indolyl)ethanedione reacted with thiosemicarbazide under atmosperic and elevated pressure to give 6-(2,5-dimethyl-3-thienyl)-5-(3-indolyl)-2,3-dihydro-1,2,4triazine-3-thione whose structure was studied in detail by the X-ray diffraction method. Reactions of 6-(2,5dimethyl-3-thienyl)-5-(3-indolyl)-2,3-dihydro-1,2,4-triazine-3-thione with amines and hydrazine resulted in formation of fused triazolo-and tetrazolotriazines. X = NH, NR.

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Crystal structure of indole derivatives

Cited by 3 publications

References 4 publications

Synthesis and Structural Evaluation of 5-Methyl-6-acetyl Substituted Indole and Gramine

Synthesis and Structural Evaluation of 5-Methyl-6-acetyl Substituted Indole and Gramine

[(5-Bromo-1H-indol-3-yl)methyl]dimethylazanium nitrate

Synthesis and Structure of 5-Indolyl-6-thienyl-1,2,4-triazines

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