Structural studies and characterization of 3-formylchromone and products of its reactions with chosen primary aromatic amines

被引:26
作者
Dziewulska-Kulaczkowska, Agnieszka [1 ]
Mazur, Liliana [1 ]
机构
[1] Marie Curie Sklodowska Univ, Dept Gen & Coordinat Chem, PL-20031 Lublin, Poland
关键词
3-Formylchromone; 4-Chromanone; FTIR spectra; X-ray analysis; TYROSINE-PHOSPHATASE; 1B; DNA-BINDING PROPERTIES; X-RAY; FORMYLCHROMONE DERIVATIVES; BIOLOGICAL-ACTIVITY; CYTOTOXIC ACTIVITY; LN(III) COMPLEXES; CHROMONES; QUINOLINES;
D O I
10.1016/j.molstruc.2010.10.049
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070305 [高分子化学与物理];
摘要
The crystal structure and FUR spectrum of 3-formylchromone (0) have been analysed. A new organic ligands, 3-(anilinomethylene)-2-methoxychroman-4-one (1) and 3-(1',4'-benzodioxan-6'-aminomethylene)-2-methoxychroman-4-one (2) were synthesized. The products of reactions between 3-formylchromone and aniline and 6-amino-1,4,-benzodioxane were studied by elemental analysis, FTIR spectroscopy, thermal analysis and X-ray crystallography. It has been found that these reactions allow to obtain derivatives of 4-chromanones from 3-formylchromone by the mechanism of nucleophilic addition, accompanied by the opening of the pyrone ring. The experimental results indicate that compounds (1) and (2) are thermal stable up to 90 and 100 degrees C, respectively. The FTIR spectra and X-ray analysis showed the present of methoxy-group in these compounds. (c) 2010 Elsevier B.V. All rights reserved.
引用
收藏
页码:233 / 242
页数:10
相关论文
共 51 条
[1]
STRUCTURES OF 3-FORMYLTHIACHROMEN-4-ONE AND 3-(CHLOROMETHYL)CHROMEN-4-ONE [J].
ADAMS, H ;
BAILEY, NA ;
GILES, PR ;
MARSON, CM .
ACTA CRYSTALLOGRAPHICA SECTION C-CRYSTAL STRUCTURE COMMUNICATIONS, 1991, 47 :1332-1334
[2]
TABLES OF BOND LENGTHS DETERMINED BY X-RAY AND NEUTRON-DIFFRACTION .1. BOND LENGTHS IN ORGANIC-COMPOUNDS [J].
ALLEN, FH ;
KENNARD, O ;
WATSON, DG ;
BRAMMER, L ;
ORPEN, AG ;
TAYLOR, R .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1987, (12) :S1-S19
[3]
The Cambridge Structural Database: a quarter of a million crystal structures and rising [J].
Allen, FH .
ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL SCIENCE, 2002, 58 (3 PART 1) :380-388
[4]
[Anonymous], 1980, Infrared Characteristic Group Frequencies
[5]
[Anonymous], 2009, SYSTEM CRYSALIS SOFT
[6]
FTIR and FTR spectral studies of 2-amino-6-bromo-3-formylchromone [J].
Arjunan, V ;
Subramanian, S ;
Mohan, S .
SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, 2004, 60 (05) :995-1000
[7]
Synthesis of coumarin derivatives from 4-oxo-4H-1-benzopyran-3-carboxaldehyde via 3-(arylaminomethylene)chroman-2,4-dione [J].
Bandyopadhyay, C ;
Sur, KR ;
Patra, R ;
Sen, A .
TETRAHEDRON, 2000, 56 (22) :3583-3587
[8]
Synthesis, molecular characterization, and biological activity of novel synthetic derivatives of chromen-4-one in human cancer cells [J].
Barve, Vivek ;
Ahmed, Fakhara ;
Adsule, Shreelekha ;
Banerjee, Sanjeev ;
Kulkarni, Sudhir ;
Katiyar, Prashant ;
Anson, Christopher E. ;
Powell, Annie K. ;
Padhye, Subhash ;
Sarkar, Fazlul H. .
JOURNAL OF MEDICINAL CHEMISTRY, 2006, 49 (13) :3800-3808
[9]
Intra- and intermolecular hydrogen bonding in 3-hydroxy- and 5-hydroxychromone [J].
Binbuga, Nursen ;
Schultz, Tor P. ;
Henry, William P. .
TETRAHEDRON LETTERS, 2008, 49 (40) :5762-5765
[10]
Solid-supported synthetic equivalents of 3-formylchromone and chromone [J].
Borrell, JI ;
Teixidó, J ;
Schuler, E ;
Michelotti, E .
TETRAHEDRON LETTERS, 2001, 42 (31) :5331-5334