2-Ethoxy-5-methylbis[1,2,4]triazolo[1,5-<i>a</i>:4′,3′-<i>c</i>]quinazoline

Al‐Salahi, Rashad; Geffken, Detlef; Bari, Ahmed

doi:10.1107/s1600536811052810

Cited by 3 publications

(2 citation statements)

References 8 publications

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“…Another feature found with 1a and 1b is the π(triazolopyri midine)···π(triazolopyrimidine) interactions. The π(triazolop yrimidine)···π(triazolopyrimidine) interactions have not been generally reported with 1,2,4-triazolo[1,5-a]pyrimidine compounds: for example, such π···π interactions while reported for 5,7-dimethyl-1,2,4-triazolo[1,5-a]pyrimidine [52] and 2, were not present in 5,7-diphenyl-1,2,4-triazolo[1,5-a]pyrimidine, 7-ethoxycarbonymethyl-5-methyl-1,2,4-triazolo[1,5-a] pyrimidine or 5-chloro-2-methylsulfonyl-1,2,4-triazolo [1,5-a] quinazoline [53][54][55][56] (16), of alternate molecules of 1c and the hydrate generated in the direction of the c axis from combinations of OW-HW2···N1, OW-HW1···N4 and N2-H2···OW intermolecular hydrogen bonds, (B) A column of molecules generated in the direction of the a axis, from π(pyrimidine)···π(chlorophenyl) and C12-Cl1··· π(triazole) interactions, (C) a chain of molecules of 1d formed in the direction of the b axis, from C9-F2··· π(pyrimidine) interactions. All interactions are drawn as dashed lines.…”

Section: Comparison With Published Structuresmentioning

confidence: 76%

“…Figure 2 shows the atom arrangements and numbering schemes for the three compounds. The bond angles and lengths within the [1,2,4]-triazolo-[1,5-a]pyrimidine fragments are all in the regions found for published compounds [52][53][54][55][56][57][58][59] and are not further discussed. Small angles are found between the pyrimidine and triazole components of the fused [1,2,4]-triazolo-[1,5-a] pyrimidine fragments: these are 2.52(13) and 1.72 (11) Interplanar angles between the best planes through the triazolopyrimidine and the chlorophenyl rings in 1a,1b and 1c are listed in Table 1.…”

Section: Molecular Structuresmentioning

confidence: 99%

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Crystal structures of two anhydrous and one hydrated 7-(arylamino)-5-methyl-2-(trifluoromethyl)-[1,2,4]-triazolo-[1,5-a]pyrimidine derivatives

Boechat

Pinheiro

Pinto

et al. 2014

Zeitschrift Für Kristallographie - Crystalline Materials

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Crystal structures of two anhydrous and one hydrated 7-(arylamino)-5-methyl-2-(trifluoromethyl)-[1,2,4]-triazolo-[1,5-a]pyrimidine derivatives Abstract: While in both 7-(arylamino)-5-methyl-2-(trifluoromethyl)-[1,2,4]-triazolo-[1,5-a]pyrimidines,1 [1a: aryl = 3,5dichlorophenyl; 1b: aryl = 2,4-dichlorophenyl), the strongest intermolecular interactions are N-H···N hydrogen bonds, different acceptor atoms are involved leading to different arrangement of molecules. In the case of 1a, N2A-H2A···N4B and N2B-H2B···N3A hydrogen bonds generate tetrameric units, composed of two molecules of each of the independent molecules, Mol A and Mol B. In the case of 1b, N2A-H2A···N4B and N2B-H2B···N4A hydrogen bonds generate C12 chains of alternate molecules A and B. As well as the strong N-H···N hydrogen bonds, there are also weaker π···π, C-X···π (X = Cl, F and H) and C-H···F interactions in 1a, and π···π, C-X···π (X = H and Cl) and C-H···X (X = F and N) interactions in 1b. In {[7-(4-chlorophenylamino)-5-methyl-2-(trifluoromethyl)-[1,2,4]-triazolo-[1,5-a]pyrimidine]. (H 2 O)}, [1c(H 2 O)], chains, C 2 2 (16) of alternate molecules of 1c and water are generated from combinations of OW-HW···N and N-H···OW intermolecular hydrogen bonds: also present are π(pyrimidine)···π(chlorophenyl), C-Cl··· π(triazole) and C-F··· π(pyrimidine) interactions. Comparisons with reported [1,2,4]-triazolo-[1,5-a]pyrimidine structures clearly show variations in the N-H···N hydrogen bonding patterns and the significant influence of the type and position of substituents on the supramolecular assemblies generated.

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Section: Comparison With Published Structuresmentioning

confidence: 76%

Section: Molecular Structuresmentioning

confidence: 99%

Crystal structures of two anhydrous and one hydrated 7-(arylamino)-5-methyl-2-(trifluoromethyl)-[1,2,4]-triazolo-[1,5-a]pyrimidine derivatives

Boechat

Pinheiro

Pinto

et al. 2014

Zeitschrift Für Kristallographie - Crystalline Materials

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An overview of triazoloquinazolines: Pharmacological significance and recent developments

Abuelizz

Al‐Salahi

2021

Bioorganic Chemistry

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Absolute configuration of (1S,2S)-3-methyl-2-phenyl-2,3-dihydrothiazolo[2,3-b]quinazolin-5-one

et al. 2012

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The absolute structure of the molecule in the crystal of the title compound, C17H14N2OS, was determined by the refinement of the Flack parameter to 0.0 (2) based on 1011 Friedel pairs. The quinazoline ring is essentially planar, with a maximum deviation of 0.037 (2) Å. The thiazole ring is distorted from planarity [maximum deviation = 0.168 (2) Å] and adopts a slightly twisted envelope conformation, with the C atom as the flap atom. The central thiazole ring makes dihedral angles of 7.01 (8) and 76.80 (10)° with the quinazoline and phenyl rings, respectively. The corresponding angle between the quinazoline and phenyl rings is 3.74 (9)°. In the crystal, there are no classical hydrogen bonds but stabilization is provided by weak C—H⋯π interactions, involving the centroids of the phenyl rings.

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2-Ethoxy-5-methylbis[1,2,4]triazolo[1,5-a:4′,3′-c]quinazoline

Cited by 3 publications

References 8 publications

Crystal structures of two anhydrous and one hydrated 7-(arylamino)-5-methyl-2-(trifluoromethyl)-[1,2,4]-triazolo-[1,5-a]pyrimidine derivatives

Crystal structures of two anhydrous and one hydrated 7-(arylamino)-5-methyl-2-(trifluoromethyl)-[1,2,4]-triazolo-[1,5-a]pyrimidine derivatives

An overview of triazoloquinazolines: Pharmacological significance and recent developments

Absolute configuration of (1S,2S)-3-methyl-2-phenyl-2,3-dihydrothiazolo[2,3-b]quinazolin-5-one

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