16864-03-2Relevant articles and documents
Recyclization of 2-imino-2H-1-benzopyrans by the action of nucleophilic reagents 4. Use of 2-(N-aroylhydrazono)coumarin-3-carboxamides for the synthesis of 3-(1,3,4-oxadiazol-2-YL)coumarins
Kovalenko,Sytnik,Nikitchenko,Rusanova,Chernykh,Porokhnyak
, p. 167 - 170 (1999)
A new method for the synthesis of 3-(1,3,4-oxadiazol-2-yl)coumarins is proposed. It is based on the recyclization of 2-(N-aroylhydrazono)coumarin-3-carboxamides, which are readily obtained by the reaction of 2-iminocoumarin-3-carboxamides with arenecarboxylic hydrazides in an acidic medium. Advantages of the given method over alternative synthetic schemes were shown. Proposals on the mechanism of reaction were made. 1999 KluwerAcademic/Plenum.
Polymorphism of 3-(5-phenyl-1,3,4-oxadiazol-2-yl)- And 3-[5-(pyridin-4-yl)-1,3,4-oxadiazol-2-yl]-2H-chromen-2-ones
Shishkina, Svitlana V.,Konovalova, Irina S.,Trostianko, Pavlo V.,Geleverya, Anna O.,Kovalenko, Sergiy M.,Bunyatyan, Natalya D.
, p. 1541 - 1553 (2019/11/14)
This study of 3-(5-phenyl-1,3,4-oxadiazol-2-yl)-2H-chromen-2-one, C17H10N2O3, 1, and 3-[5-(pyridin-4-yl)-1,3,4-oxadiazol-2-yl]-2H-chromen-2-one, C16H9ON3O3, 2, was performed on the assumption of the potential anticancer activity of the compounds. Three polymorphic structures for 1 and two polymorphic structures for 2 have been studied thoroughly. The strongest intermolecular interaction is stacking of the 'head-to-head' type in all the studied crystals. The polymorphic structures of 1 differ with respect to the intermolecular interactions between stacked columns. Two of the polymorphs have a columnar or double columnar type of crystal organization, while the third polymorphic structure can be classified as columnar-layered. The difference between the two structures of 2 is less pronounced. Both crystals can be considered as having very similar arrangements of neighbouring columns. The formation of polymorphic modifications is caused by a subtle balance of very weak intermolecular interactions and packing differences can be identified only using an analysis based on a study of the pairwise interaction energies.
Synthesis of 3-(5-phenyl-1, 3,4-oxadiazol-2-yl)-2H-chromen-2-ones as anticonvulsant agents
Naga Sudha,Girija Sastry,Sai Harika,Yellasubbaiah
, p. 737 - 745 (2019/05/22)
3-(5-Phenyl-l,3,4-oxadiazol-2-yl)-2H-chromen-2-one (IVa-IVl) have been synthesized from N-benzylidene2-oxo-2#- chromene-3-carbohydrazide (IIIa-IIIl). The structure of synthesized coumarinyl oxadiazoles have been established by spectral data, elemental ana
Synthesis and biological evaluation of 2,5-disubstituted 1,3,4-oxadiazole derivatives with both COX and LOX inhibitory activity
Akhter, Mymoona,Akhter, Nayeema,Alam,Zaman,Saha, Rikta,Kumar
experimental part, p. 767 - 776 (2012/04/04)
Dual cyclooxygenase/lipoxygenase (COX/LOX) inhibitors constitute a valuable alternative to classical nonsteroidal anti-inflammatory drugs (NSAIDs) and selective COX-2 inhibitors for the treatment of inflammatory diseases. A series of 3-(5-phenyl/phenylami
Microwave accelerated solvent-free synthesis of 1,3,4-oxadiazoles using polymer supported dehydration reagent
Li, Zheng,Yu, Jinlan,Ding, Runbo,Wang, Zhiyuan,Wang, Xicun
, p. 2981 - 2986 (2007/10/03)
2-Aryl-5-(coumarin-3′-yl)-1,3,4-oxadiazoles are efficiently synthesized by microwave accelerated solvent-free procedure in high yield via the condensation of coumarin-3-carboxylic acid with (un)substituted benzoic acid hydrazides using poly(ethylene glyco
A new pathway to 3-hetaryl-2-oxo-2H-chromenes: On the proposed mechanisms for the reaction of 3-carbamoyl-2-iminochromenes with dinucleophiles
Kovalenko, Sergiy M.,Bylov, Igor E.,Sytnik, Konstantyn M.,Chernykh, Valentyn P.,Bilokin, Yaroslav V.
, p. 1146 - 1165 (2007/10/03)
The present account summarizes the author's studies to elucidate the mechanisms of the recently reported rearrangements resulting from inter- and/or intramolecular reactions of 2-imino-2H-chromene-3-carboxamides with different dinucleophiles.
Recyclization of 2-imino-2H-1-benzopyrans under the influence of nucleophilic reagents. 1. New approach to the synthesis of 3-(1,3,4-oxadi-, thiadi-, and triazolyl-2)coumarins
Kovalenko,Zubkov,Chernykh,Turov,Ivkov
, p. 163 - 168 (2007/10/03)
It has been found that under the action of hydrazides of carboxylic acids, 2-iminocoumarin-3-carboxamides are recydized to N(1)-acylamidrazones of coumarin-3-carboxylic acids. The use of N(1)-acylamidrazones is proposed as a simple and effective means of synthesizing 3-(1,3,4-oxadi-, thiodi-, and triazolyl-2)coumarins. The possibilities of alternate schemes of synthesis are discussed, and a mechanism is suggested for the recyclization. 1996 Plenum Publishing Corporation.
Coumarin congeners as antidepressants
Singh,Srivastava,Palit,Shanker
, p. 993 - 996 (2007/10/02)
3-Carboethyl coumarin (I) was converted to coumarin 3-acid hydrazide (II). This on reaction with appropriate aldehyde yielded 3-arylidino amino coumarin (III). Compound III on diazotisation and reaction with ferric chloride yielded the corresponding formazans viz. 3-substituted phenyl azoarylidino, amido coumarins (IVa1-a10) and oxadiazoles viz. 2-aryl-5-(3-coumarinyl)-1,3,4-oxadiazoles (Va1-a3), respectively. Simultaneously 3-carboethyl coumarin on hydrolysis gave 3-carboxy coumarin (VI) which on reaction with aryl amine in methylene chloride yielded 3-(N-aryl)amido coumarin (VIIa1-a3). The compounds were screened for their antidepressant activity against a tricyclic antidepressant (imipramine). Compounds IVa4, IVa5 and IVa9 exhibited activity better than imipramine with no toxicity (ALD50 > 1000 mg/kg) but IVa5 showed some side effects.
