Heterocycles from heterocycles. 1,3-Diaryl-4,5-imidazolidinediones from 1,3,5-triarylhexahydro-1,3,5-triazines and oxalyl chloride

Verardo, Giancarlo; Giumanini, Angelo G.; Gorassini, Fausto; Tolazzi, Marilena; Strazzolini, Paolo

doi:10.1016/s0040-4020(01)81552-0

Cited by 15 publications

(3 citation statements)

References 22 publications

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“…The oxamide group in compound 1 has the structure of two independently amides disregarding a π conjugation across the central C᎐C bond as is shown by the oxalyl OC᎐CO average bond length value of 1.541(5) Å (1.53 Å in other examples). 16 The structures showed a OC᎐CO torsion angle value of 180.0(2)Њ for a trans conformation in contrast with other oxamides which show a torsional angle between 90Њ and 115Њ. 16 The oxalyl 11 presents the same characteristic values 6) C( 3)᎐C( 4) C( 4)᎐C( 5) C( 6)᎐C( 5) C( 7 2)᎐N( 9) C( 3)᎐C( 4)᎐C( 5) C( 6)᎐C( 5)᎐C( 4) O( 7)᎐C( 7)᎐C(7A) C( 7)᎐N( 9)᎐C( 2) N( 9)᎐C( 7 10)᎐C( 1)᎐C( 6) C( 6)᎐C( 1)᎐C( 2) C( 3)᎐C( 2)᎐C( 1) C( 1)᎐C( 2)᎐N( 9) C( 1)᎐C( 6)᎐C( 5) O( 8)᎐C( 7)᎐N( 9) N( 12)᎐C( 7)᎐O( 13 12)᎐C( 7) O( 9)᎐C( 10) O( 14)᎐C( 8) O( 15)᎐C( 16) C(...…”

Section: X-ray Diffraction Analysismentioning

confidence: 99%

“…16 The structures showed a OC᎐CO torsion angle value of 180.0(2)Њ for a trans conformation in contrast with other oxamides which show a torsional angle between 90Њ and 115Њ. 16 The oxalyl 11 presents the same characteristic values 6) C( 3)᎐C( 4) C( 4)᎐C( 5) C( 6)᎐C( 5) C( 7 2)᎐N( 9) C( 3)᎐C( 4)᎐C( 5) C( 6)᎐C( 5)᎐C( 4) O( 7)᎐C( 7)᎐C(7A) C( 7)᎐N( 9)᎐C( 2) N( 9)᎐C( 7 10)᎐C( 1)᎐C( 6) C( 6)᎐C( 1)᎐C( 2) C( 3)᎐C( 2)᎐C( 1) C( 1)᎐C( 2)᎐N( 9) C( 1)᎐C( 6)᎐C( 5) O( 8)᎐C( 7)᎐N( 9) N( 12)᎐C( 7)᎐O( 13 12)᎐C( 7) O( 9)᎐C( 10) O( 14)᎐C( 8) O( 15)᎐C( 16) C( 1)᎐C( 6) C(3)᎐C(4) C( 5)᎐C(…”

Section: X-ray Diffraction Analysismentioning

confidence: 99%

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Three-center intramolecular hydrogen bonding in oxamide derivatives. NMR and X-ray diffraction study

Martínez‐Martínez

Padilla‐Martínez²,

Brito³

et al. 1998

J. Chem. Soc., Perkin Trans. 2

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This contribution describes the synthesis and structural investigation of the symmetric and nonsymmetric oxamides N,N Ј-bis(2-hydroxyphenyl)oxamide 1, N,N Ј-bis(5-tert-butyl-2-hydroxyphenyl)oxamide 2, N,N Ј-bis(3,5-dimethyl-2-hydroxyphenyl)oxamide 3, N,N Ј-bis(2-hydroxybenzyl)oxamide 4, N,N Ј-diphenethyloxamide 5, N-(2-hydroxyphenyl)-N Ј-(2-methoxyphenyl)oxamide 6, N-(2-hydroxyphenyl)-N Ј-phenethyloxamide 7, (1S,2R)-(؊)-N-(2-hydroxyphenylcarbamoylcarbonyl)norephedrine 8, (1R,2S)-(؊)-N-(2-hydroxyphenylcarbamoylcarbonyl) 9, ethyl N-(2-hydroxyphenyl)oxalamate 10 and ethyl N-(2-methoxyphenyl)oxalamate 11. The structures were established by 1 H, 13 C, 15 N and variable temperature NMR spectroscopy. Compounds 1-4 and 6-11 are stabilized by intramolecular three-center hydrogen bonding between the amide proton and two oxygen atoms. The 1 H NMR / T value of the amide proton correlates with the 15 N NMR chemical shift. The X-ray diffraction molecular structures of 1 and 11 showed a planar conformation with trans configuration in the solid state, corresponding to the preferred conformation found in solution.

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Section: X-ray Diffraction Analysismentioning

confidence: 99%

Section: X-ray Diffraction Analysismentioning

confidence: 99%

Three-center intramolecular hydrogen bonding in oxamide derivatives. NMR and X-ray diffraction study

Martínez‐Martínez

Padilla‐Martínez²,

Brito³

et al. 1998

J. Chem. Soc., Perkin Trans. 2

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“…Recently, 2,5-imidazolidinedione derivatives were prepared as histone deacetylase 6 (HDAC6) selective inhibitors for various human diseases, including diverse neurodegenerative diseases and cancer [13]. However, there are very few reports on the synthesis of 4,5-imidazolidinedione compounds [14][15][16]. We report herein the synthesis of a hybrid compound 3, thieno [2,3-d]pyrimidine derivative bearing a 4,5-imidazolidinedione moiety.…”

Section: Introductionmentioning

confidence: 99%

1,3-Bis(5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-4-yl)imidazolidine-4,5-dione

Yin

Kim

Song

2022

Molbank

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A thieno[2,3-d]pyrimidine derivative 3 bearing a 4,5-imidazolidinedione moiety, 1,3-bis(5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-4-yl)imidazolidine-4,5-dione, was efficiently synthesized in 66% yield by the reaction of N,N′-bis(5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-4-yl)methanediamine 2 with oxalyl chloride in the presence of pyridine in refluxing dichloroethane for 10 h. The structure of the new synthesized compounds was fully characterized by 1H, 13C NMR, IR spectroscopy, mass-spectrometry and elemental analysis.

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17O NMR studies on ?-diamides

Cerioni

Giumanini

Verardo

1998

J. Phys. Org. Chem.

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Heterocycles from heterocycles. 1,3-Diaryl-4,5-imidazolidinediones from 1,3,5-triarylhexahydro-1,3,5-triazines and oxalyl chloride

Cited by 15 publications

References 22 publications

Three-center intramolecular hydrogen bonding in oxamide derivatives. NMR and X-ray diffraction study

Three-center intramolecular hydrogen bonding in oxamide derivatives. NMR and X-ray diffraction study

1,3-Bis(5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-4-yl)imidazolidine-4,5-dione

17O NMR studies on ?-diamides

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