Synthesis of Some New Imidazo[4,5-B]Pyridine Derivatives Using 2-Cyanomethyl-1-Methyl-1H-Imidazo[4,5-B]Pyridine

Abstract

The reactions of 2-cyanomethyl-1-methyl-1H-imidazo[4,5-b]pyridine with isothiocyanates, nitroso compounds, acid chlorides, and thioglycolic acid were investigated. New imidazo[4,5-b]pyridine derivatives with various substituents in 2-position and derivatives of the new pyrrolo[2′,1′:2,3]imidazo[4,5-b]pyridine ring system were synthesized. The compounds obtained were tested in vitro for their tuberculostatic activity.     

2-Ethanethioamide in Heterocyclic Synthesis: Synthesis and Characterization of Several New Pyridine and Fused Azolo- and Azinopyridine Derivatives

Pyridine-2(1H)-thione derivatives 3a,b were synthesized from the reaction of 1-(phenyl-sulfanyl)acetone (1) and cinnnamonitrile derivatives 2a,b. Compounds 3a,b reacted with different halogenated reagents 7a–f to give 2-S-alkylpyridine derivatives 8a–l, which could be, in turn, cyclized into the corresponding thieno[2,3-b]pyridine derivatives 9a–l. Compounds 9d,j reacted with acetic anhydride, formic acid, carbon disulfide, phenyl isothiocyanate, and nitrous acid to yield the corresponding pyrido[3′,2′:4,5]thieno[2,3-d]pyrimidine 12a,b, 15a,b, 17a,b, 20a,b, and pyrido[3′,2′:4,5]thieno[2,3-d][1,2,3]triazinone derivatives 22a,b, respectively.

Supplemental materials are available for this article. Go to the publisher's online edition of Phosphorus, Sulfur, and Silicon and the Related Elements to view the free supplemental file.     

Synthesis and Antioxidant,Anti-Inflammatory,and Analgesic Activity of Novel Polycyclic Pyrimido[4,5-b]quinolines

The behavior of the 2-methylthio-pyrimido[4,5-b]quinolin-4-one towards differently substituted amines is reported. Also, the reactivity of 3-aminothiazolo[3′,2′ :1,2]-pyrimido[4,5-b]quinoline-2-carbonitrile towards formic acid, urea, thiourea, formamide, and carbon disulfide is discussed. Some of the synthesized derivatives possess biological activities as anti-inflammatory and analgesic agents. Some of these selective biologically active compounds were screened for antioxidant properties.     

Synthesis of New Pyrido[2′,3′:3,4]pyrazolo[1,5-a]pyrimidines and Their Use in the Preparation of Tetraheterocyclic Systems

8,10-Dimethyl-3-(unsubstituted, methyl, ethyl, n-butyl, phenyl)-4-hydroxypyrido[2′,3′:3,4]pyrazolo[1,5-a]pyrimidin-2(1H)-ones and 3-(2-hydroxyethyl)-2,8,10-trimethylpyrido[2′,3′:3,4]pyrazolo[1,5-a]pyrimidin-4-ol were synthesized by cyclocondensation of 3-amine-4,6-dimethyl-1H-pyrazolo[3,4-b]pyridine with ethyl malonates and α-acetyl-γ-butyrlolactone. Dichloro- and diazido- derivatives were obtained from the reaction of pyridopyrazlopyrimidine derivatives with POCl₃ followed by NaN₃. The tetrahetrocyclic systems were formed by cyclization of 4-chloro-3-(2-chloroethyl)-2,8,10-trimethylpyrido[2′,3′:3,4]pyrazolo[1,5-a]pyrimidine with the appropriate primary amines. The structures of all compounds were established by NMR and mass spectra.     

BENZOQUINOLINES II. SYNTHESIS OF SOME NEW BENZO[h] PYRIMIDO [4′,5′:4,5]THIENO[2,3-b]QUINOLINE DERIVATIVES AND RELATED FUSED HEXACYCLIC SYSTEMS

Abstract

Reaction of 8-amino-7-(2 furyl)-5,6-dihydrobenzo[h]thieno[2,3-b]quinoline-9-carbonitrile (3a) with phenyl isothiocyanate, triethyl orthoformate, ethylenediamine and/or sodium azide afforded benzo[h]thieno[2,3-b]quinolines 4,7,20 and 25 respectively. Cyclization of thiourea derivative 4 furnished thioxopyrimidine derivative 5. The dithioxopyrimidine 6 was prepared by reaction of 3a with carbon disulfide. On treatment of 7 with hydrazine hydrate, 10-amino-7-(2-furyl)-11-imino-5,6,10,11-tetrahydrobenzo[h]pyrimido[4′,5′:4,5]thieno [2,3-b]quinoline (8) was obtained. Compounds 8,20 and 25 were used as key intermediates in the synthesis of the fused hexacyclic compounds 9–19, 21–24 and 26–28 respectively. 8-Amino-7-(2-furyl)-5,6-dihydrobenzo[h]thieno[2,3-b]quinoline-9-carboxamide (3b) was reacted with some reagents, namely triethyl orthoformate, benzaldehyde, carbon disulfide, phenyl isothiocyanate, and/or acetic anhydride to give the corresponding benzo[h]pyrimido [4′,5′: 4,5]thieno[2,3-b]quinolines 29, 30, 31, 32 and 34. Compound 29 underwent some sequence reactions to give 37–42. Some of the prepared compounds were tested in vitro for their antibacterial and antifungal activities.     

Reactions of quinones with some amino alcohols,thiols and a UV-Vis study

Abstract

In the present study, the reactions of 2,3-dichloro-1,4-naphthoquinone (DCNQ) with amino-1,2-propanediol and some thiols were investigated. Novel N-, N,S-, and S,O- substituted derivatives were obtained and the structures of all compounds were characterized by spectroscopic methods (FT-IR, ¹H NMR, ¹³ Baker, R. A.; Tatum, J. H.; Nemec, S. Antimicrobial Activity of Naphthoquinones from Fusaria. Mycopathologia 1990, 111, 9–15. DOI: 10.1007/BF02277294.[Crossref], [PubMed], [Web of Science ®] , [Google Scholar]C NMR, Mass spectroscopy) and microanalysis. The absorption behaviors of novel compounds were also investigated with UV-Vis spectroscopy in different solvents, such as ethanol, tetrahydrofuran and chloroform.     

Addition reactions of a phosphorus triamide to nitrosoarenes and acylpyridines

Abstract

Tricoordinate phosphorus compounds react with a wide variety of double bonds through addition reactions. The dipolar and cyclic products formed are important intermediates in organophosphorus chemistry. We investigated the reactivity between phosphorus triamide 1 and nitrosoarenes and 2-acylpyridines. For sterically congested substrates, the formation of σ⁵ Aroyan, C. E.; Dermenci, A.; Miller, S. J. The Rauhut–Currier Reaction: A History and Its Synthetic Application. Tetrahedron 2009, 65, 4069–4084. DOI: 10.1016/j.tet.2009.02.066.[Crossref], [Web of Science ®] , [Google Scholar],λ⁵-phosphorus products is observed. DFT calculations indicate this product is formed through a concerted [4?+?1] mechanism. For less sterically congested substrates, products are observed arising from cleavage of the N?=?O or C?=?O bond with formation of a terminal P?=?O bond and aryl nitrene or carbene migration into a P–N bond of the phosphorus triamide core. DFT calculations are consistent with an initial [2?+?1] addition to phosphorus followed by formal carbene/nitrene migration in these cases.     

Synthesis and antimicrobial activity of new derivatives of pyrano[4',3':4',5']pyrido[3',2':4,5]thieno[3,2-d]pyrimidine and new heterocyclic systems

Taking into account previously obtained biological results on some polyheterocyclic compounds (containing different heteroatoms) and in particular on several 8-amino-5-isopropyl-2,2-dimethyl-10-(methylthio)-1,4-dihydro-2H-pyrano[4’’,3’’:4’,5’]pyrido[3’,2’:4,5]thieno[3,2-d]pyrimidines Ia-v we have carried out the synthesis of twentyone 8-amino-5-isobutyl-2,2-dimethyl-10-(methylthio)-1,4-dihydro-2H-pyrano[4’’,3’’:4’,5’]pyrido[3’,2’:4,5]thieno[3,2-d]pyrimidines 6. Therefore we have slightly modified the structure of the previously studied I introducing at C-5 an isobutyl group instead of the previously examined isopropyl ones in order to see if this variation (changing a little the lipophilicity) will affect the biological activity. Furthermore thieno[3,2-d]pyrimidine-8-thione 7 and their S-alkylated 8 were synthesized. Finally by alkylation of 5-isobutyl-2,2-dimethyl-10-thioxo-1,4,10,11-tetrahydro-2H-pyrano[4'',3'':4',5']pyrido[3',2':4,5]thieno[3,2-d]pyrimidin-8(9H)-one 3 with alkyl dichlorides (bifunctional reagents) we realized the cyclization of a thiazole or thiazine ring on the [b] side of the pyrimidine ring with formation of the new condensed pentaheterocyclic systems: pyrano[4'',3'':4',5']pyrido[3',2':4,5]thieno[3,2-d][1,3]thiazolo[3,2-a]pyrimidin-8-one 11 and pyrano[4''',3''':4'',5'']pyrido[3'',2'':4',5']thieno[3',2':4,5]pyrimido[2,1-b][1,3]thiazin-8-one 12. It was found that some of the synthesized compounds showed interesting antimicrobial activity (by agar diffusion method) against some gram-positive and gram-negative bacilli strains.     

Synthesis of Some New Thieno[2,3-b]pyridines,Pyrimidino[4′,5′:4,5]thieno[2,3-b]-pyridines,and 2,3-Dihydro-1,3,4-thiadiazoles

Thieno[2,3-b]pyridines were synthesized from 6-benzofuran-2-yl-4-phenyl-2-sulfanylpyridine-3-carbonitrile and each of chloro acetone, ethyl chloroacetate, ω -bromoacetophenone, and chloroacetonitrile. These compounds were conveniently converted into novel pyrido[4′,5′:4,5]thieno[3,2-d]pyrimidines. Also, 2,3-dihydro-1,3,4-thiadiazole was synthesized from hydrazonoyl halides and 2-benzofuran-2-yl-3-(phenylamino)-3-thioxopropanenitrile. The structures of the products have been elucidated by elemental analyses, spectral data studies, and alternative syntheses whenever possible. The newly synthesized compounds were tested towards microorganisms.     

Facile and Convenient Synthesis of Pyrazole,Pyridine, Pyridazine,Pyrazolo[3,4-b]pyridine,and Pyrazolo[5,1-c][1,2,4]triazine Derivatives

Abstract

A convenient synthesis of a series of pyrazole, pyridine, pyridinethione, pyridazine, pyrazolo[3,4-b]pyridine, imidazo[1,2-a]pyrimidine, and pyrazolo[5,1-c][1 Kumar , R. 5-(1-Substituted)alkyl pyrimidine nucleosides as antiviral (herpes) agents . Curr. Med. Chem. 2004 , 11 , 2749 – 2766 . [Google Scholar] 2 Holy , A. ; Günter , J. ; Dvoráková , H. ; Masojídková , M. ; Andrei , G. ; Snoeck , R. ; Balzarini , J. ; De Clercq , E. Structure–antiviral activity relationship in the series of pyrimidine and purine N-[2-(2-phosphonomethoxy)ethyl] nucleotide analogues, 1: Derivatives substituted at the carbon atoms of the base . J. Med. Chem. 1999 , 42 , 2064 – 2086 . [Google Scholar] 4 Brandes , W. ; Daum , W. ; Krauss , P. Fungicidal oxime ethers. Ger. Patent 2,623,847, 1977; Chem. Abstr . 1978 , 88 , 120822h . [Google Scholar]]triazine derivatives incorporating a pyrimidine moiety, via the reactions of the versatile, readily accessible 3-oxo-N-(pyrimid-2-yl)butanamide with the appropriate reagents, is described.     

1,3-Disubstitutedpyrazole-4-caboxaldehyde in Heterocyclic Synthesis: A Novel Synthesis of Pyridine-2(1H)-thione and Fused Nitrogen and/or Sulfur Heterocyclic Derivatives

Pyridine-2(1H)-thione 5 was synthesized from the reaction of 3-[3-(4-chlorophenyl)-1-phenyl-1H-pyrazol-4-yl]-1-phenylpropenone (3) and cynothioacetamide (4). Compound 5 reacted with halogented compounds 6a–e to give 2-S-alkylpyridine derivatives 7a–e, which could be in turn cyclized into the corresponding thieno[2,3-b]-pyridine derivatives 8a–e. Compound 8a reacted with hydrazine hydrate to give 9. The latter compound reacted with acetic anhydride (10a), formic acid (10b), acetic acid, ethyl acetoacetate, and pentane-2,4-dione to give the corresponding pyrido[3′,2′:4,5]thieno-[3,2-d]pyrimidine 13a,b, pyrazolo[3′,4′:4,5]thieno[3,2-d]pyridine 14 and thieno[2,3-b]-pyridine derivatives 18 and 20, respectively. Alternatively, 8c reacted with 10a,b and nitrous acid to afford the corresponding pyrido[3′,2′:4,5]thieno[3,2-d]pyrimidine 24a,b and pyrido[3′,2′:4,5]thieno[3,2-d][1,2,3]triazine 26 derivatives, respectively. Finally compound 5 reacted with methyl iodide to give 2-methylthiopyridine derivative 27, which could be reacted with hydrazine hydrate to yield the corresponding pyrazolo[3,4-b]-pyridine derivative 29.     

Green Method for the Synthesis of Benzo[f]pyrimido[4,5-b]quinoline Derivatives Catalyzed by Iodine in Aqueous Media

A convenient one-pot synthesis of benzo[f]pyrimido[4,5-b]quinoline derivatives is described via three-component reaction of benzaldehydes, naphthalen-2-amine, and barbituric acid at room temperature in aqueous media catalyzed by iodine. Compared with other methods, this three-component reaction used a green solvent, gave good yields, and was operationally simple.     

SYNTHESIS OF 15H-ISOQUINO[2′,3′:3,4]IMIDAZO[2,1-B]QUINAZOLINE-7,13,15-TRIONES AND 14H-ISOQUINO[2′,3′:3,4]IMIDAZO[2,1-B]BENZO[G]QUINAZOLINE-8,14,16-TRIONE AS NEW POLYCYCLIC FUSED-RING SYSTEMS

3-Thioxo-2H-imidazo[1,5-b]isoquinoline-1,5-dione (3) and 2-sub-stituted 3-thioxo-2H-imidazo[1,5-b]isoquinoline-1,5-diones (4a–l) were prepared from the reaction of 2-thiohydantoin (2) and 3-substituted 2-thiohydantoin (5a–l) with 2-formyl benzoic acid (1). Alkylation of 3 under an anhydrous basic conditions afforded 4a–i. The alkylation of 3 in aqueous basic solution afforded 3-(alkylmercapto)imidazo[1,5-b]isoquinoline-1,5-diones (7a,b). Reactions of the aromatic amino acids 9a,b and 12 with 7a afforded 2-(2H-1,5 dioxoimidazo[1,5-b]isoquinazolin-3-ylideneamino)benzoic acids (10a, b) and 3-(2H-1,5-dioxoimidazo[1,5-b]isoquinazolin-3-ylideneamino)2-naphthalenecarboxylic acid (13), which were then cyclyzed by heating in acetic anhydride to afford 15H-isoquino[2′,3′ :3,4] imidazo[2,1-b]quinazoline-7,13,15-triones (11a,b) and 14H-isoquino[2′,3′:3,4]imidazo[2,1-b]benzo[g]quinazoline-8,14,16-trione (14). Some of the new compounds were tested for their antitumor activities.     

[2]Benzothiophene bent-shaped liquid crystals

New liquid crystalline (LC) compounds containing the [2 Weissflog, W., Nádasi, H., Dunemann, U., Pelzl, G., Diele, S., Eremin, A. and Kresse, H. 2001. J. Mater. Chem., 11: 2748–2758. [Crossref], [Web of Science ®] , [Google Scholar]]benzothiophene chromophore unit have been synthesised and their mesomorphic properties studied. Mesomorphic and fluorescent properties have been modified by various chemical moieties. Among others, terminal fluoroalkyl and/or chiral chains were introduced to stabilise mesophases and support the formation of polar phases. In spite of the bent shape due to the central 1,3-diphenylbenzo[c]thiophene unit, all compounds exhibit phases typical for the rod-like LC: nematic, smectic A and smectic C or their chiral analogues using the chiral (S)-C₂H₅CH(CH₃)(CH₂)₆CO or (S)-C₁₀H₂₁OCH(CH₃)CO chain. The orientational order in the nematic phase was studied by polarised infrared measurements. The fluorescent properties of the studied compounds have been measured and their parameters established.     

Synthesis,crystal structure,vibrational, optical properties,and a theoretical study of a new Pb(II) complex with bis(1-methylpiperazine-1,4-diium): [C5H14N2]2PbCl6·3H2O

An investigation of the solid-state X-ray structure of the new organic–inorganic compound [C₅H₁₄N₂]₂PbCl₆·3H₂O shows a layered organization of the (PbCl₆)^4– anions, with (R₂NH₂)⁺ groups and water molecules developed in the [001 A. Hu, H.L. Ngo, W. Lin. J. Am. Chem. Soc., 125, 11490 (2003).[Crossref], [PubMed], [Web of Science ®] , [Google Scholar]] plane at x = (2n?+?1)/4. The crystal structure is stabilized by N???H···Cl, N???H···O, O???H···Cl, O???H···O, and C???H···Cl hydrogen bonds. The powder X-ray diffraction and X-ray photoelectron spectroscopic (XPS) analyses confirm the phase purity of the crystal sample. The intermolecular contacts are quantified using the Hirshfeld surfaces computational method. The major inter-contacts contributing to the Hirshfeld surfaces are H…Cl, H…H, and O…H. The vibrational modes were identified and assigned by IR and Raman spectroscopies. The optical properties were investigated by UV–visible and photoluminescence spectroscopic studies. The compound was characterized by thermal analysis to determine its thermal behavior with respect to the temperature. Finally, X-ray photoelectron spectroscopy analysis is reported for analyzing the surface chemistry of [C₅H₁₄N₂]₂PbCl₆·3H₂O.     

One‐pot Sequential Reactions Featuring a Copper‐catalyzed Amination Leading to Pyrido[2′,1′:2,3]imidazo[4,5‐c]quinolines and Dihydropyrido[2′,1′:2,3]imidazo[4,5‐c]quinolines

Tetracyclic skeletons combining an imidazo[1,2‐a]pyridine moiety with a quinoline framework such as pyrido[2′,1′:2,3]imidazo[4,5‐b]quinoline are stimulating increasing interests since they are close isosteres of a series of powerful antiproliferative compounds. In this paper, we report a novel methodology for the synthesis of pyrido[2′,1′:2,3]imidazo[4,5‐c]quinolines through one‐pot sequential reactions of commercially available or readily obtainable 2‐aminopyridines, 2‐bromophenacyl bromides, aqueous ammonia, and aldehydes. Moreover, dihydropyrido[2′,1′:2,3]imidazo[4,5‐c]quinolines could also be obtained in a similar manner by using various ketones as the substrates in place of aldehydes. Notably, the whole procedure combines condensation/amination/cyclization reactions in one pot to give complex compounds in a simple and practical manner. Compared with literature methods, the synthetic strategy reported herein has the advantages of readily available starting materials, structural diversity of products, good functional group tolerance, and obviation of step‐by‐step operations.     

Synthesis and Properties of 6-Amino-7-hetaryl-5-R-5H-pyrrolo[2,3-b]pyrazine-2,3-dicarbonitriles

We have established that when 5-chloro-6-[cyano(2,3-dihydro-1-R-benzo[d]azol-2-yl)methyl]-2,3-pyrazinedicarbonitriles are reacted with nucleophilic reagents (aliphatic and aromatic amines, hydrogen sulfide), annelation of the five-membered ring occurs on the [b] face of the pyrazine with formation of 6-amino-7-hetaryl-5-R-5H-pyrrolo[2,3-b]pyrazine-2,3-dicarbonitriles and 6-amino-7-(1H-benzo[d]imidazol-2-yl)thieno[2,3-b]pyrazine-2,3-dicarbonitrile respectively. Further heating with excess of acylating reagent leads to formation of a novel heterocyclic system 1H-benzo[4,5]imidazo[1,2-c]pyrazino[2',3':4,5]pyrrolo[3,2-e]pyrimidine. Reaction of vicinal dinitriles with hydrazine hydrate leads to the novel system 1H-pyrrolo[2',3':5,6]pyrazino[2,3-d]pyridazine.     

Glycolic acid-supported cobalt ferrite-catalyzed one-pot synthesis of pyrimido[4,5-b]quinoline and indenopyrido[2,3-d]pyrimidine derivatives

Herein, one-pot synthesis of pyrimido[4,5-b]quinoline and indenopyrido[2,3-d]pyrimidine derivatives was developed by the three-component reaction of aldehydes, 6-amino-1,3-dimethyluracil, and 1,3-dicarbonyl compounds in the presence of glycolic acid-supported cobalt ferrite CoFe₂O₄@SiO₂@Si (CH₂)₃NHCOOCH₂COOH as a novel magnetic catalyst in ethanol at reflux conditions. Glycolic acid-supported cobalt ferrite was characterized via Fourier transform infrared spectroscopy (FT-IR), X-ray diffraction (XRD), thermogravimetric analysis (TGA), scanning electron microscopy (SEM), transmission electron microscopy (TEM), energy-dispersive X-ray spectroscopy (EDX), and vibrating sample magnetometer (VSM). Moreover, the catalyst was easily recovered with magnetic separation and recycled at least for five times without significant loss of its catalytic activity. The products were formed in excellent yields over appropriate reaction times under environmentally friendly conditions. The high efficiency and easy isolation of catalyst from products with an external permanent magnet are some of the remarkable advantages of this method.     

Synthesis of Some N1-(3-Hydroxy-2-pyridyl)benzamides

Benzoxazoles are of special interest because of having various types of biological properties such as antihistaminic, antihelmintic antifungal and antibacterial activities. ¹ Hisano, T., Ichikawa, M., Tsumoto, K. and Tasaki, M. 1982. Chem. Pharm. Bull, 30: 2996 [CSA][Crossref], [Web of Science ®] , [Google Scholar], ² Prudhomme, M., Guyot, J. and Jeminet, G. 1986. J. Antibiotics, 39: 934 [CSA][Crossref], [PubMed], [Web of Science ®] , [Google Scholar], ³ Ersan, S., Nacak, S., Berkem, R. and Özden, T. 1997. Arzneim. Forsch, 47: 963 [CSA][PubMed], [Web of Science ®] , [Google Scholar], ⁴ Sener, E., Yalc?n, ?., Temeiz, Ö., Ören, ?., Ak?n, A. and Ucartürk, N. 1997. Farmaco, 52: 99 [CSA][PubMed] , [Google Scholar], ⁵ Ören, ?., Temiz, Ö., Yalc?n, ?., Sener, E., Ak?n and Ucartürk, N. 1997. Forsch, 47: 1393 [CSA] [Google Scholar], ⁶ Temiz, Ö., Ören, ?., Sener, E., Yalc?n, ?. and Ucartürk, N. 1998. Farmaco, 53: 337 [CSA][CROSSREF][Crossref], [PubMed] , [Google Scholar], ⁷ Yalc?n, ?., Ören, ?., Sener, E., Ak?n, A. and Ucartürk, N. 1992. J. Med. Chem, 27: 401 [CSA][CROSSREF][Crossref], [Web of Science ®] , [Google Scholar], ⁸ Temiz, Ö., Ören, ?. and Altanlar, N. 2002. Farmaco, 57: 175 [CSA][CROSSREF][Crossref], [PubMed] , [Google Scholar], ⁹ Sener, E., Temeiz, Ö., Yalc?n, ?. and Altanlar, N. 2000. Farmaco, 55: 397 [CSA][CROSSREF][Crossref], [PubMed] , [Google Scholar], ¹⁰ Ören, ?., Temiz, Ö., Yalc?n, ?., Sener, E. and Altanlar, N. 1998. Eur. J. Pharm. Sci., 7: 153 [CSA][Crossref], [Web of Science ®] , [Google Scholar] Benzamide derivatives, as the possible metabolites of benzoxazoles, show various types of biological activities. ¹¹ Sener, E., Bingöl, K., Ören, ?., Arpac?, Ö., Yalc?n, K. ?. and Altanlar, N. 2000. Farmaco, 55: 469 [CSA][CROSSREF][Crossref], [PubMed] , [Google Scholar], ¹² Sener, E., Yalc?n, K. ?. and Altanlar, N. 2002. Farmaco, 57: 451 [CSA][CROSSREF][Crossref], [PubMed] , [Google Scholar] Some N-(2-hydroxyphenyl)- benzamides, which showed significant activity compared to phenylacetamides and furamides,11 have been synthesized by treating 2-aminophenol with carboxylic acid chlorides under weak basic solution. ¹¹ Sener, E., Bingöl, K., Ören, ?., Arpac?, Ö., Yalc?n, K. ?. and Altanlar, N. 2000. Farmaco, 55: 469 [CSA][CROSSREF][Crossref], [PubMed] , [Google Scholar], ¹² Sener, E., Yalc?n, K. ?. and Altanlar, N. 2002. Farmaco, 57: 451 [CSA][CROSSREF][Crossref], [PubMed] , [Google Scholar] However, synthesis and especially biological activity of N-(3-hydroxy-2-pyridyl)benzamides were not studied well. Owing to the versatility of benzamides we have extended the reaction of 2-amino-3-pyridinol with different carboxylic acid chlorides in order to preparation of some new benzamide derivatives containing a hydroxypyridyl ring.