Synthesis of Biologically Active Thiazolo‐benzopyranyl‐s‐triazine Derivatives.

Mulwad, V. V.; Shirodkar, Jyoti M.

doi:10.1002/chin.200324136

Cited by 12 publications

(21 citation statements)

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“…The trans positions of the protons on C(4) and C(5) in pyrazolinone 7a were confirmed by X-ray crystallography (Figure 1, Table 3). The five-membered ring in molecule 7a is planar within the limits of experimental error, despite the two tetrahedral atoms C(4) and C (5). The three phenyl rings of the molecule are also planar.…”

Section: _______mentioning

confidence: 73%

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Synthesis and reactions of 4-(arylhydrazino)coumarins

Strakova

Strakovs

Петрова

et al. 2009

Chem Heterocycl Comp

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Keywords: 4-(arylhydrazino)coumarins, 1-aryl-3-(2-hydroxyphenyl)-2H-pyrazin-5-ones, aromatic aldehydes, 2,3-diaryl[1]benzopyrano [4,3-b]pyrazol-4-ones.In a development of work on the synthesis of coumarins with heterocycles at the C(3)-C(4) bond [1-3] we have synthesized pyrazolocoumarins by the reactions of 4-(arylhydrazino)coumarins with aromatic aldehydes. We reverted to pyrazolocoumarins [4-6] which, like other 3,4-heteroannelated coumarins, were observed to have biological activity [7][8][9][10][11][12][13].The reactions of phenyl-, 2-chlorophenyl-and 4-bromophenylhydrazine hydrochlorides with 4-hydroxycoumarin 1 in the presence of triethylamine were carried out by heating in the absent of solvent (1h 30 min, 90-100ºC). In all cases, 1-aryl-3-(2-hydroxyphenyl)pyrazol-5-ones 3a-c were formed along with the corresponding 4-(arylhydrazino)coumarins 2a-c. Pyrazolone 3a was obtained previously [14] by boiling 4-hydroxycoumarin with phenylhydrazine in benzene. On boiling the same reagents in toluene with a catalytic amount of p-toluenesulfonic acid we obtained 4-(phenylhydrazino)coumarin (2a) as the main product (50%) and the pyrazolone 3a in a yield of only 18%. Boiling the pyrazolones 3a-c in acetic anhydride in the presence of p-toluenesulfonic acid gave the diacetyl derivatives 4a-c.The reaction of (4-arylhydrazino)coumarins 2a-c with 4-chlorobenzaldehyde in DMF solution in the presence of equimolar catalytic amounts of piperidine and acetic acid gave the corresponding 2-aryl-3-(4-chlorophenyl)[1]benzopyrano[4,3-b]pyrazol-4-ones 5a-c.

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Section: _______mentioning

confidence: 73%

“…We reverted to pyrazolocoumarins [4][5][6] which, like other 3,4-heteroannelated coumarins, were observed to have biological activity [7][8][9][10][11][12][13].…”

mentioning

confidence: 98%

Synthesis and reactions of 4-(arylhydrazino)coumarins

Strakova

Strakovs

Петрова

et al. 2009

Chem Heterocycl Comp

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“…Reaction of hydrazide 22 with the appropriate aromatic aldehydes gave the arylidenehydrazinocarbonyl 23, which on condensation with thioglycolic acid in dry benzene gave thiazolidinone derivatives 24 [63][64][65][66]. …”

Section: Acid Hydrazidesmentioning

confidence: 99%

Progress in the chemistry of 4‐ thiazolidinones

Hamama

Ismail

Shaaban

et al. 2008

Journal of Heterocyclic Chem

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“…Many Schiff's bases are known to be medicinally important and are used to design medicinal compounds [2]. They are well known intermediated for the preparation of azetidinone [3], thiazolidinone [4], formazone [5], arylacetamide [6], metal complexes [7][8][9] and many other derivatives [10][11]. Many reagent have been used for the synthesis of optically active imines such as Lewis acids [12], MnO 2 [13], CaO [14], ZnCl 2 [15], P 2 O 5 :SiO 2 [16], infrared [17], ultrasound radiation [18] and fly-ash:H 2 SO 4 [19] with microwave irradiation.…”

Section: Introductionmentioning

confidence: 99%

Synthesis, Spectral Correlations and Biological Activities of Some (E)-[4-(Substituted Benzylidene Amino)Phenyl] (Phenyl) Methanones

Mayavel

Thirumurthy

Dineshkumar

et al. 2014

ILCPA

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A series of Schiff's bases have been synthesized by fly-ash:p-toluenesulfonic acid (fly-ash:PTS) catalyzed microwave assisted oxidative coupling of arylamines and substituted benzaldehydes under solvent-free condition. The synthesized Schiff's bases are characterized by their physical constants, analytical and spectroscopic data. The group frequencies of imines such as IR (, cm -1 ) and NMR (, ppm) spectral data was correlated with Hammett substituent constants, F and R parameters using single and multi-linear regression analysis. The antimicrobial activities of these Schiff's bases have been studied using Bauer-Kirby method.

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Synthesis of Biologically Active Thiazolo‐benzopyranyl‐s‐triazine Derivatives.

Cited by 12 publications

References 0 publications

Synthesis and reactions of 4-(arylhydrazino)coumarins

Synthesis and reactions of 4-(arylhydrazino)coumarins

Progress in the chemistry of 4‐ thiazolidinones

Synthesis, Spectral Correlations and Biological Activities of Some (E)-[4-(Substituted Benzylidene Amino)Phenyl] (Phenyl) Methanones

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