X-ray structural investigation of tricyclic 2,3-tetra and 2,3-pentamethylene-3,4-dihydroquinazol 4-ones and their derivatives

Tashkhodzhaev, B.; Turgunov, K. K.; D'yakonov, A. L.; Belova, G. A.; Shakhidoyatov, Kh. M.

doi:10.1007/bf01165198

Cited by 2 publications

(2 citation statements)

References 11 publications

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“…The crystal structures were used as starting geometries [1: TEFDEN (Tashkhodzhaev et al, 1995)…”

Section: Quantum Chemical Calculations -Conformational Study and Natural Bonding Orbital Analysismentioning

confidence: 99%

“…Like the parent molecules, the synthesized compounds and their new ylidene, bromo and formyl derivatives have pronounced antibacterial and cytotoxic activities. The aim of this work is to quantify the chemical reactivity of mackinazolinone derivatives by introducing different substituents at position 2 of alkaloid mackinazolinone (1) (CCDC refcode TEFDEN; Tashkhodzhaev et al, 1995) (see Fig. 1).…”

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confidence: 99%

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Structural insight from intermolecular interactions and energy framework analyses of 2-substituted 6,7,8,9-tetrahydro-11H-pyrido[2,1-b]quinazolin-11-ones

Tojiboev¹,

Элмурадов²,

Mouhib³

et al. 2021

Acta Crystallogr Sect B

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The crystal structures of three mackinazolinone derivatives (2-amino-6,7,8,9-tetrahydro-11H-pyrido[2,1-b]quinazolin-11-one at room temperature, and 2-nitro-6,7,8,9-tetrahydro-11H-pyrido[2,1-b]quinazolin-11-one and N-(11-oxo-6,8,9,11-tetrahydro-7H-pyrido[2,1-b]quinazolin-2-yl)benzamide at 100 K) are explored using X-ray crystallography. To delineate the different intermolecular interactions and the respective interaction energies in the crystal architectures, energy framework analyses were carried out using the CE-B3LYP/6-31G(d,p) method implemented in the CrystalExplorer software. In the structures the different molecules are linked by C—H...O, C—H...N and N—H...O hydrogen bonds. Together with these hydrogen bonds, C—H...π and C—O...π interactions are involved in the formation of a three-dimensional crystal network. A Hirshfeld surface analysis allows the visualization of the two-dimensional fingerprint plots and the quantification of the contributions of H...H, H...C/C...H and H...O/O...H contacts throughout the different crystal structures. To obtain additional information on the intrinsic properties of our targets and to compare the experimental crystal structures with their respective conformations in the gas phase, quantum chemical calculations at the B3LYP-D3BJ/6-311++G(d,p) level of theory, including Grimme's D3 correction term and BJ damping functions, were carried out to account for intramolecular dispersion interactions. The identified energy gaps between the highest occupied and the lowest unoccupied molecular orbitals (HOMO–LUMO gap) of our targets in the gas phase and in two implicit solvents (methanol and dimethyl sulfoxide) allow us to quantify the impact of different substituents on the reactivity of mackinazolinone derivatives.

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“…The crystal structures were used as starting geometries [1: TEFDEN (Tashkhodzhaev et al, 1995)…”

Section: Quantum Chemical Calculations -Conformational Study and Natural Bonding Orbital Analysismentioning

confidence: 99%

mentioning

confidence: 99%

Structural insight from intermolecular interactions and energy framework analyses of 2-substituted 6,7,8,9-tetrahydro-11H-pyrido[2,1-b]quinazolin-11-ones

Tojiboev¹,

Элмурадов²,

Mouhib³

et al. 2021

Acta Crystallogr Sect B

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6,7,8,9,10,11-Hexahydro-13H-azocino[2,1-b]quinazolin-13-one

et al. 2009

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The title compound, C14H16N2O, is a synthetic analogue of quinazolone alkaloids with pyrrilo, pyrido and azopino rings. The quinazolinic part of the molecule is generally planar within 0.037 (3) Å; the eight-membered ring exhibits an intermediate conformation between the chair and boat forms as it is typical for cyclooctene rings. An ethylene group of the azopino ring is disordered over two positions with a refined occupancy ratio of 0.910 (7):0.090 (7). In the crystal, the H atoms of the aromatic rings form weak C—H⋯O and C—H⋯N hydrogen bonds. One C—H⋯O hydrogen bond leads to the formation of a one-dimensional chain. Another C—H⋯O and a C—H⋯N bond link these chains, generating a three-dimensional network.

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X-ray structural investigation of tricyclic 2,3-tetra and 2,3-pentamethylene-3,4-dihydroquinazol 4-ones and their derivatives

Cited by 2 publications

References 11 publications

Structural insight from intermolecular interactions and energy framework analyses of 2-substituted 6,7,8,9-tetrahydro-11H-pyrido[2,1-b]quinazolin-11-ones

Structural insight from intermolecular interactions and energy framework analyses of 2-substituted 6,7,8,9-tetrahydro-11H-pyrido[2,1-b]quinazolin-11-ones

6,7,8,9,10,11-Hexahydro-13H-azocino[2,1-b]quinazolin-13-one

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