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Synthesis, Cyclization and Nucleophilic Substitution Reactions of Substituted Pyrazole Carboxylic Acid

Yıl 2022, Cilt: 12 Sayı: 1, 279 - 286, 01.03.2022

İsrafil Tozlu Volkan Taşdemir Aycan Güner Hasan Genç

https://doi.org/10.21597/jist.948269

Öz

Substituted pyrazole carboxylic acid 2a-b derivatives, obtained from 2,3-furandione 1 and benzaldehyde hydrazone 11a-b was converted via reactions of its acid chloride 3a-b. The corresponding ester 6a-b, urea 7a-b, and amide derivatives 4a-b, 8a-b were obtained from the reaction of the acyl chloride of the pyrazole carboxylic acid with various alcohols, urea, and amines. Additionally, the corresponding nitrile derivatives 5 were obtained by extracting water from the amide derivatives (SOCl2 / DMF). Furthermore, cyclization reactions of substituted pyrazole carboxylic acid derivatives using hydrazine were investigated 9 and reaction of 2b decarboxylation product 10.

Anahtar Kelimeler

cyclization decarboxylation pyrazole carboxylic acid pyrazole

Kaynakça

  • Akçamur Y, Penn G, Ziegler E, Sterk H, Kollenz G, Peters K, Peters E.M, 1986. Reactions of Cyclic Oxalyl Compounds. Reaction of 4-benzoyl-5-phenyl-furan-2,3-dione with Phenylhydrazones and Phenylhydrazıne. Monatsh Chemistry, 117, 231-245.
  • Akçamur Y, Şener A, Ipekoglu A.M, Kollenz G, 1997. Functionalization and Cyclization Reactions of 4-Benzoyl-1,5-diphenyl- 1H-pyrazole-3-carboxylic Acid. Journal Heterocyclic Chemistry, 34, 221-224.
  • Baird M.S, 2003. Thermally Induced Cyclopropene−Carbene Rearrangements: An Overview. Chemical Reviews, 103(4):1271-1294.
  • Banks R.E, Smart S.E, Tatlow J.C, 1994. Organofluorine Chemistry.Principles and Commercial Applications: New York, Plenum: 52-200.
  • Bildirici İ, Şener A, Atalan E, Battal A, Genç H, 2009. Synthesis and Antibacterial Activity of 4-benzoyl-1-(4-carboxy-phenyl)-5-phenyl-1H-pyrazole-3-carboxylic Acid and Derivatives. Medicinal Chemistry Research, 18(5):327-340.
  • Frizzo C. P, Villetti M.A, Tier A.Z, Gindri I.M, Buriol L, Rosa F.A, Claramunt R.M, Sanz D, Martins M.A.P, 2013. Structural and thermodynamic properties of new pyrazolo[3,4-d]pyridazinones. Thermochimicaacta. 574, 63-72.
  • Genç H, 2009. Reaction of 4-Ethoxycarbonyl-5-phenyl-2,3-dihydro-2,3-furandione with Some Hydrazine Nucleophiles. Asian Journal of Chemistry, 21(1):299-303.
  • Genç H, Tan M, Gümüş S, Mengeş N, Bildirici İ, Şener A, 2010. Studies on the different reaction pathways between 3-Acetyl-5-benzoyl-6- methyl-2-phenyl-4H-pyran-4-one and alkylamines. Bulletin of Korean Chemical Society, 31(9):2633-2636.
  • Genç H, Taşdemir V, Tozlu İ, Öğün E, 2019. Synthesis of Novel Tetra-Substituted Pyrazole Derivatives from 2,3-Furandione. Letters in Organic Chemistry, 16(11):891-897.
  • Hagmann W. K, 2008. The Many Roles for Fluorine in Medicinal Chemistry. Journal of Medicinal Chemistry, 51(15):4359-4369.
  • Harper D. B, O'Hagan D, Murphy C. B, 2003. Fluorinated Natural Products: Occurrence and Biosynthesis. Natural Production of Organohalogen Compounds; Handbook of Environmental Chemistry: Berlin, Heidelberg, Springer, 141.
  • Joule J. A, Mills K, 2010. Heterocyclic Chemistry, Blackwell. Oxford. 1-150.
  • Kamal A, Visweswarasastry K. N, Chandrasekhar D, Mani G.S, Adiyala P.R, Nanubolu J.B, Singarapu K.K, Andmaurya R.A, 2015. One-Pot, Three-Component Approach to the Synthesis of 3,4,5-Trisubstituted Pyrazoles. The Journal of Organic Chemistry, 80(9):4325-4335.
  • Kappe C. O, Terpetschnig E, Penn G, Kollenz G, Peters K, Peter E. M, 1995. Substituent effect on the site of nucleophilic attack at 1H-pyrrole-2,3-diones. Liebigs Annalen der Chemie, 3, 537-543.
  • Korkusuz E, Yıldırım İ, 2011. On the Reactions of Furan-2,3-diones with Oxindole (=1,3-Dihydro-2H-indol-2-one) and Lawesson Reagent. Synthesis of New 1,3-Dihydro-2H-indol-2-ones, Bis-furanones, and Bis-pyrrolones. Helvetica, 94(5):801-810.
  • Mahajan R.N, Havaldar F.H, Fernandes P.S, 1991. Syntheses and biological activity of heterocycles derived from 3-methoxy-1-phenyl-1H-pyrazole-5-carboxylate. Indian Chemical Society, 68, 245-246.
  • Matyus P, 1998. 3(2H)-Pyrıdazınones-Some Recent Aspects Of Synthetıc And Medicinal Chemistry. J. Heterocyclic Chemistry, 35,1075.
  • Shawali A.S, 1977. Synthesis and tautomeric structure of some 2H-pyrazolo[3,4-d]pyridazines. Journal of Heterocyclic Chemistry, 14, 375-381.
  • Şener A, Kasımoğulları R, Şener M. K, Bildirici İ, Akçamur Y, 2002. Studies on the reactions of cyclicoxalyl compounds with hydrazines or hydrazones II [1]:Synthesis and reactions of 4-benzoyl-1-(3-nitrophenyl)-5- phenyl-1H-pyrazole-3-carboxylic acid. Journal of Heterocyclic Chemistry, 39(1):869-875.
  • Şener A, Genc H, Tozlu I, Sener M. K, 2004. Studies on the Reactions of 4-Ethoxycarbonyl-5-phenyl-2,3-dihydro-2,3- furandione with Some NH Nucleophiles. Turkis Journal of Chemistry, 28(5):659-665.
  • Şener A, Kasimogullari R, Sener M.K, Genç H, 2004. Studies on reactions of cyclic oxalyl compounds with hydrazines or hydrazones. 2. Synthesis and reactions of 4-benzoyl-1-(4-nitrophenyl)-5-phenyl-1H-pyrazole-3-carboxylic acid. Chemistry of Heterocyclic Compounds, 40(8):1039-1046.
  • Şener A, Tozlu İ, Genç H, Bildirici İ, Arısoy K, 2007. Synthesis and some reactions of 4-(ethoxycarbonyl)-1,5-diphenyl-1H-pyrazole-3-carboxylic acid. Journal of Heterocyclic Chemistry, 44(5):1077-1081.
  • Şener A, Eskinoba S, Bildirici İ, Genç H, Kasımoğulları R, 2007. A study on chemical behaviors of some 4-pyrones synthesized by one-step reactions towards various amines. Journal of Heterocyclic Chemistry, 44, 337-341.
  • Şener A, Mengeş N, Akkurt M, Karaca S, Büyükgüngör, O, 2008. Efficient synthesis of some oxalacetic acid and pyruvic acid derivatives from the reactions of 2, 3-furandiones with 2-phenylindole. Tetrahedron Letters, 49(17):2828-2831.
  • Şener A, Bildirici İ, Genç H, Mengeş N, Eskinoba S, 2008. One Step Synthesis of Some 2,5,6-Trisubstituted-1,3-Dioxin-4-ones. Turkish Journal of Chemistry, 32(1):19-24.
  • Yılırım I, Saripinar E, Güzel Y, Patat S, Akçamur Y, 1995. Theoretical investigations on the mechanism of interaction of 4-formyl furan-2,3-dion and urea. Journal of Molecular Structure: THEOCHEM, 334(2):165-171.
  • Yıldırım İ, Kandemirli F, Korkusuz E, 2005. Experimental And Theoretical Studies On The Functionalization Reaction Of 4- Benzoyl -1,5- Diphenyl-1h-Pyrazole-3- Carboxylic Acid And Chloride With 2,3- Diaminopyridine. Molecules. 10(3):559-571.
  • Taslimi P, Türkan F, Cetin A, Burhan H, Karaman M, Bildirici I, Gulçin İ, Şen F, 2019. Pyrazole[3,4-d]pyridazine derivatives: Molecular docking and explore of acetylcholinesterase and carbonic anhydrase enzymes inhibitors as anticholinergics potentials. Biyoorganic Chemistry, 92,103213.
  • Tewari A. K, Mishra A, 2001. Synthesis and anti-inflammatory activities of N4, N5-disubstituted-3-methyl-1H-pyrazolo[3,4-c]Pyridazines. Bioorganic and Medicinal Chemistry, 9(3):715-718.
  • Tozlu I, Hacıalioğlu E, Taşdemir V, Genç H, 2019. Synthesis and Some Reactions of Pyrazole-3-carboxylic acid Having Trifluoromethyl Unit. Gümüşhane Üniversitesi Fen Bilimleri Enstitüsü Dergisi, 9(4):645-654.

Sübstitüe Pirazol Karboksilik Asit Sentezi, Siklizasyonu ve Nükleofilik Yer Değiştirme Reaksiyonları

Yıl 2022, Cilt: 12 Sayı: 1, 279 - 286, 01.03.2022

İsrafil Tozlu Volkan Taşdemir Aycan Güner Hasan Genç

https://doi.org/10.21597/jist.948269

Öz

Substitüe pirazol karboksilik asit 2a-b türevleri 2,3-furandion 1 ve benzaldehit hidrazon 11a-b elde edildi. Pirazol karboksilik asit türevleri asit klorürlerine 3a-b dönüştürüldü. Pirazol karboksilik asitin asit klorürü çeşitli alkoller, üre ve aminlerle reaksiyonundan karşılık gelen ester 6a-b, üre 7a-b ve amid 4a-b, 8a-b türevleri elde edildi. Ek olarak, amid türevlerinden (SOCl2/DMF) ile su çekilerek karşılık gelen nitril türevleri 5 elde edildi. Ayrıca pirazol karboksilik asit türevlerinin hidrazin ile siklizasyon reaksiyonlarından 9 ve dekarboksilasyonu sonucu 10 türevlerinin eldesi reaksiyonları araştırılmıştır.

Anahtar Kelimeler

Siklizasyon dekarboksilasyon pirazol karboksilit asit pirazol

Kaynakça

  • Akçamur Y, Penn G, Ziegler E, Sterk H, Kollenz G, Peters K, Peters E.M, 1986. Reactions of Cyclic Oxalyl Compounds. Reaction of 4-benzoyl-5-phenyl-furan-2,3-dione with Phenylhydrazones and Phenylhydrazıne. Monatsh Chemistry, 117, 231-245.
  • Akçamur Y, Şener A, Ipekoglu A.M, Kollenz G, 1997. Functionalization and Cyclization Reactions of 4-Benzoyl-1,5-diphenyl- 1H-pyrazole-3-carboxylic Acid. Journal Heterocyclic Chemistry, 34, 221-224.
  • Baird M.S, 2003. Thermally Induced Cyclopropene−Carbene Rearrangements: An Overview. Chemical Reviews, 103(4):1271-1294.
  • Banks R.E, Smart S.E, Tatlow J.C, 1994. Organofluorine Chemistry.Principles and Commercial Applications: New York, Plenum: 52-200.
  • Bildirici İ, Şener A, Atalan E, Battal A, Genç H, 2009. Synthesis and Antibacterial Activity of 4-benzoyl-1-(4-carboxy-phenyl)-5-phenyl-1H-pyrazole-3-carboxylic Acid and Derivatives. Medicinal Chemistry Research, 18(5):327-340.
  • Frizzo C. P, Villetti M.A, Tier A.Z, Gindri I.M, Buriol L, Rosa F.A, Claramunt R.M, Sanz D, Martins M.A.P, 2013. Structural and thermodynamic properties of new pyrazolo[3,4-d]pyridazinones. Thermochimicaacta. 574, 63-72.
  • Genç H, 2009. Reaction of 4-Ethoxycarbonyl-5-phenyl-2,3-dihydro-2,3-furandione with Some Hydrazine Nucleophiles. Asian Journal of Chemistry, 21(1):299-303.
  • Genç H, Tan M, Gümüş S, Mengeş N, Bildirici İ, Şener A, 2010. Studies on the different reaction pathways between 3-Acetyl-5-benzoyl-6- methyl-2-phenyl-4H-pyran-4-one and alkylamines. Bulletin of Korean Chemical Society, 31(9):2633-2636.
  • Genç H, Taşdemir V, Tozlu İ, Öğün E, 2019. Synthesis of Novel Tetra-Substituted Pyrazole Derivatives from 2,3-Furandione. Letters in Organic Chemistry, 16(11):891-897.
  • Hagmann W. K, 2008. The Many Roles for Fluorine in Medicinal Chemistry. Journal of Medicinal Chemistry, 51(15):4359-4369.
  • Harper D. B, O'Hagan D, Murphy C. B, 2003. Fluorinated Natural Products: Occurrence and Biosynthesis. Natural Production of Organohalogen Compounds; Handbook of Environmental Chemistry: Berlin, Heidelberg, Springer, 141.
  • Joule J. A, Mills K, 2010. Heterocyclic Chemistry, Blackwell. Oxford. 1-150.
  • Kamal A, Visweswarasastry K. N, Chandrasekhar D, Mani G.S, Adiyala P.R, Nanubolu J.B, Singarapu K.K, Andmaurya R.A, 2015. One-Pot, Three-Component Approach to the Synthesis of 3,4,5-Trisubstituted Pyrazoles. The Journal of Organic Chemistry, 80(9):4325-4335.
  • Kappe C. O, Terpetschnig E, Penn G, Kollenz G, Peters K, Peter E. M, 1995. Substituent effect on the site of nucleophilic attack at 1H-pyrrole-2,3-diones. Liebigs Annalen der Chemie, 3, 537-543.
  • Korkusuz E, Yıldırım İ, 2011. On the Reactions of Furan-2,3-diones with Oxindole (=1,3-Dihydro-2H-indol-2-one) and Lawesson Reagent. Synthesis of New 1,3-Dihydro-2H-indol-2-ones, Bis-furanones, and Bis-pyrrolones. Helvetica, 94(5):801-810.
  • Mahajan R.N, Havaldar F.H, Fernandes P.S, 1991. Syntheses and biological activity of heterocycles derived from 3-methoxy-1-phenyl-1H-pyrazole-5-carboxylate. Indian Chemical Society, 68, 245-246.
  • Matyus P, 1998. 3(2H)-Pyrıdazınones-Some Recent Aspects Of Synthetıc And Medicinal Chemistry. J. Heterocyclic Chemistry, 35,1075.
  • Shawali A.S, 1977. Synthesis and tautomeric structure of some 2H-pyrazolo[3,4-d]pyridazines. Journal of Heterocyclic Chemistry, 14, 375-381.
  • Şener A, Kasımoğulları R, Şener M. K, Bildirici İ, Akçamur Y, 2002. Studies on the reactions of cyclicoxalyl compounds with hydrazines or hydrazones II [1]:Synthesis and reactions of 4-benzoyl-1-(3-nitrophenyl)-5- phenyl-1H-pyrazole-3-carboxylic acid. Journal of Heterocyclic Chemistry, 39(1):869-875.
  • Şener A, Genc H, Tozlu I, Sener M. K, 2004. Studies on the Reactions of 4-Ethoxycarbonyl-5-phenyl-2,3-dihydro-2,3- furandione with Some NH Nucleophiles. Turkis Journal of Chemistry, 28(5):659-665.
  • Şener A, Kasimogullari R, Sener M.K, Genç H, 2004. Studies on reactions of cyclic oxalyl compounds with hydrazines or hydrazones. 2. Synthesis and reactions of 4-benzoyl-1-(4-nitrophenyl)-5-phenyl-1H-pyrazole-3-carboxylic acid. Chemistry of Heterocyclic Compounds, 40(8):1039-1046.
  • Şener A, Tozlu İ, Genç H, Bildirici İ, Arısoy K, 2007. Synthesis and some reactions of 4-(ethoxycarbonyl)-1,5-diphenyl-1H-pyrazole-3-carboxylic acid. Journal of Heterocyclic Chemistry, 44(5):1077-1081.
  • Şener A, Eskinoba S, Bildirici İ, Genç H, Kasımoğulları R, 2007. A study on chemical behaviors of some 4-pyrones synthesized by one-step reactions towards various amines. Journal of Heterocyclic Chemistry, 44, 337-341.
  • Şener A, Mengeş N, Akkurt M, Karaca S, Büyükgüngör, O, 2008. Efficient synthesis of some oxalacetic acid and pyruvic acid derivatives from the reactions of 2, 3-furandiones with 2-phenylindole. Tetrahedron Letters, 49(17):2828-2831.
  • Şener A, Bildirici İ, Genç H, Mengeş N, Eskinoba S, 2008. One Step Synthesis of Some 2,5,6-Trisubstituted-1,3-Dioxin-4-ones. Turkish Journal of Chemistry, 32(1):19-24.
  • Yılırım I, Saripinar E, Güzel Y, Patat S, Akçamur Y, 1995. Theoretical investigations on the mechanism of interaction of 4-formyl furan-2,3-dion and urea. Journal of Molecular Structure: THEOCHEM, 334(2):165-171.
  • Yıldırım İ, Kandemirli F, Korkusuz E, 2005. Experimental And Theoretical Studies On The Functionalization Reaction Of 4- Benzoyl -1,5- Diphenyl-1h-Pyrazole-3- Carboxylic Acid And Chloride With 2,3- Diaminopyridine. Molecules. 10(3):559-571.
  • Taslimi P, Türkan F, Cetin A, Burhan H, Karaman M, Bildirici I, Gulçin İ, Şen F, 2019. Pyrazole[3,4-d]pyridazine derivatives: Molecular docking and explore of acetylcholinesterase and carbonic anhydrase enzymes inhibitors as anticholinergics potentials. Biyoorganic Chemistry, 92,103213.
  • Tewari A. K, Mishra A, 2001. Synthesis and anti-inflammatory activities of N4, N5-disubstituted-3-methyl-1H-pyrazolo[3,4-c]Pyridazines. Bioorganic and Medicinal Chemistry, 9(3):715-718.
  • Tozlu I, Hacıalioğlu E, Taşdemir V, Genç H, 2019. Synthesis and Some Reactions of Pyrazole-3-carboxylic acid Having Trifluoromethyl Unit. Gümüşhane Üniversitesi Fen Bilimleri Enstitüsü Dergisi, 9(4):645-654.
Toplam 30 adet kaynakça vardır.

Ayrıntılar

Birincil Dil İngilizce
Konular Kimya Mühendisliği
Bölüm Kimya / Chemistry
Yazarlar

İsrafil Tozlu 0000-0002-9402-2539

Volkan Taşdemir 0000-0001-5836-784X

Aycan Güner Bu kişi benim 0000-0002-6333-4353

Hasan Genç 0000-0003-1454-3279

Yayımlanma Tarihi 1 Mart 2022
Gönderilme Tarihi 5 Haziran 2021
Kabul Tarihi 10 Kasım 2021
Yayımlandığı Sayı Yıl 2022 Cilt: 12 Sayı: 1

Kaynak Göster

APA Tozlu, İ., Taşdemir, V., Güner, A., Genç, H. (2022). Synthesis, Cyclization and Nucleophilic Substitution Reactions of Substituted Pyrazole Carboxylic Acid. Journal of the Institute of Science and Technology, 12(1), 279-286. https://doi.org/10.21597/jist.948269
AMA Tozlu İ, Taşdemir V, Güner A, Genç H. Synthesis, Cyclization and Nucleophilic Substitution Reactions of Substituted Pyrazole Carboxylic Acid. Iğdır Üniv. Fen Bil Enst. Der. Mart 2022;12(1):279-286. doi:10.21597/jist.948269
Chicago Tozlu, İsrafil, Volkan Taşdemir, Aycan Güner, ve Hasan Genç. “Synthesis, Cyclization and Nucleophilic Substitution Reactions of Substituted Pyrazole Carboxylic Acid”. Journal of the Institute of Science and Technology 12, sy. 1 (Mart 2022): 279-86. https://doi.org/10.21597/jist.948269.
EndNote Tozlu İ, Taşdemir V, Güner A, Genç H (01 Mart 2022) Synthesis, Cyclization and Nucleophilic Substitution Reactions of Substituted Pyrazole Carboxylic Acid. Journal of the Institute of Science and Technology 12 1 279–286.
IEEE İ. Tozlu, V. Taşdemir, A. Güner, ve H. Genç, “Synthesis, Cyclization and Nucleophilic Substitution Reactions of Substituted Pyrazole Carboxylic Acid”, Iğdır Üniv. Fen Bil Enst. Der., c. 12, sy. 1, ss. 279–286, 2022, doi: 10.21597/jist.948269.
ISNAD Tozlu, İsrafil vd. “Synthesis, Cyclization and Nucleophilic Substitution Reactions of Substituted Pyrazole Carboxylic Acid”. Journal of the Institute of Science and Technology 12/1 (Mart 2022), 279-286. https://doi.org/10.21597/jist.948269.
JAMA Tozlu İ, Taşdemir V, Güner A, Genç H. Synthesis, Cyclization and Nucleophilic Substitution Reactions of Substituted Pyrazole Carboxylic Acid. Iğdır Üniv. Fen Bil Enst. Der. 2022;12:279–286.
MLA Tozlu, İsrafil vd. “Synthesis, Cyclization and Nucleophilic Substitution Reactions of Substituted Pyrazole Carboxylic Acid”. Journal of the Institute of Science and Technology, c. 12, sy. 1, 2022, ss. 279-86, doi:10.21597/jist.948269.
Vancouver Tozlu İ, Taşdemir V, Güner A, Genç H. Synthesis, Cyclization and Nucleophilic Substitution Reactions of Substituted Pyrazole Carboxylic Acid. Iğdır Üniv. Fen Bil Enst. Der. 2022;12(1):279-86.