Synthesis of new 5-aryl pyrido [3', 2': 4, 5] thieno [2, 3-e] [1, 2, 3, 4] tetrazolo [1, 5-c] pyrimidine derivatives

Synthesis of new 5-aryl pyrido [3', 2': 4, 5] thieno [2, 3-e] [1, 2, 3, 4] tetrazolo [1, 5-c] pyrimidine derivatives

Few pyrido [3', 2': 4, 5] thieno [2, 3-e][1, 2, 3, 4] tetrazolo [1, 5-c] pyrimidines are $known^{1-4}$ but, to the best of our knowledge, none of their 5-aryl derivatives has been reported in the literature. The routes to these compounds are limited and start from suitably substituted pyridothienopyrimidines either through diazotization of their hydrazino derivative with sodiumn itrite in acetic $acid^{1,4}$ or by the reaction of their chloro compound with sodium azide in ethanol or $acetonitrile^{1,3,4}$ In connection with our interest in the chemistry of fused thienopyridines, we reported a convenient synthesis of pyrido [3', 2': 4, 5] thieno [3, 2-d] pyrimidine-4(3H)-ones from ethyl-3-amino [2, 3-b] pyridine-2 carboxylate through heterocyclization with aryl $nitriles.^5$ In continuation of this work and due to our interest in the synthesis of fused $heterocycles^{5-13}$ we report herein a facile one-step synthesis of new 5-arylpyridothieno tetrazolopyrimidine derivatives (2a-f ).

___

  • 1. S.W. Schneller and F.W. Clough, J. Heterocyclic Chem. 11, 175 (1970).
  • 2. W. Seth and N.M. Kanna, Indian. J. Chem. Sect B. 14, 335 (1976).
  • 3. Lokhan and O.P. Singh, Arch. Pharm. 228 (1985).
  • 4. W. Schneller and F.W. Clough, J. Heterocyclic Chem. 11, 975-977 (1974).
  • 5. Roshani, A. Davoodnia , M.Sh. Hedayat and M. Bakavoli, Phosphorus, Sulfur, and Silicon., 179, 1153 (2004).
  • 6. Bakavoli, A. Davoodnia, M. Rahimizadeh and M.M. Heravi, Mendeleev Communications, 16 (1), 29 (2006).
  • 7. Bakavoli, A. Davoodnia, M. Rahimizadeh, M.M. Heravi and M. Ghassemzadeh, J. Chem. Res. (S), 178 (2002).
  • 8. Bakavoli, A. Davoodnia, M. Rahimizadeh and M.M. Heravi, Phosphorus, Sulfur, and Silicon, 177, 2303 (2002).
  • 9. Bakavoli, M. Nikpour and M. Rahimizadeh, Phosphorus, Sulfur, and Silicon, 180, 2265 (2005)
  • 10. Bakavoli, B. Reihani, M. Rahimizadeh and M. Nikpour, Phosphorus, Sulfur, and Silicon, 181, 99 (2006).
  • 11. Davoodnia, M. Bakavoli, A. Vahedinia, M. Rahimizadeh and M. Roshani, Heterocycles, 68, 801 (2006).
  • 12. M. Heravi, M. Bakherad, M. Rahimizadeh, M. Bakavoli and M. Ghassemzadeh, Heterocyclic Commun, 10, 335 (2004).
  • 13. M. Heravi, A. Kivanloo, M. Rahimizadeh, M. Bakavoli, B. Neumuller and M. Ghassemzadeh, Tetrahedron Letter, 46, 1607 (2005).
  • 14. K. Ciszewski, L. Celewicz and K. Golankiewicz, Synthesis, 777 (1995).
Turkish Journal of Chemistry-Cover
  • ISSN: 1300-0527
  • Yayın Aralığı: Yılda 6 Sayı
  • Yayıncı: TÜBİTAK
Sayıdaki Diğer Makaleler

Preconcentration of Trace Elements on Amberlite XAD-4 Resin Functionalised with 1,2-bis (o-aminophenylthio) Ethane and Their Determination by FAAS in Environmental Samples

Ömer DALMAN, Volkan Numan BULUT

A Convenient and Efficient Synthesis of N-Acylsulfonamides in the Presence of Silica Phosphoric Acid under Heterogeneous and Solvent-Free Conditions

Ahmad Reza MASSAH, Mina DABAGH, Maryam AFSHAR, Ahmad Reza MOMENI

Preconcentration of trace elemets on amberlite XAD-4 resin functionalised with 1,2- bis (0-aminophenylthio) ethane and their determination by FAAS in environmental samples

Ömer DALMAN, Mehmet TÜFEKÇİ, Volkan Numan BULUT, İsmail DEĞİRMENCİOĞLU

Synthesis of new 5-aryl pyrido [3', 2': 4, 5] thieno [2, 3-e] [1, 2, 3, 4] tetrazolo [1, 5-c] pyrimidine derivatives

Abolghasem DAVOODNIA, Mehdi BAKAVOLI, Mahsan BASHASH, Mina ROSHANI, Rahele ZHIANI

Fused Heterocycles: Synthesis of Some New Imidazopyridines as Anti-Mycobacterial Agents

Birgül Özden KASIMOĞULLARI, Zafer CESUR

Synthesis of New 5-Aryl Pyrido [3´, 2´: 4, 5] Thieno [2, 3-e] [1, 2, 3, 4] Tetrazolo [1, 5-c}] Pyrimidine Derivatives

Abolghasem DAVOODNIA, Mehdi BAKAVOLI, Mahsan BASHASH

Synhesis of piperazine based polyimide in the presence of ionic liquids

Turgay SEÇKİN, Bülent ALICI, Süleyman KÖYTEPE

Synthesis and Isolation of 1-Cyclohex-1,2-dien-1-ylbenzene from 1-(2-Iodocyclohex-1-en-1-yl)benzene and 1-(2-Iodocyclohex-2-en-1-yl)benzene

Mustafa CEYLAN, Yakup BUDAK, M. Burcu GÜRDERE

Synthesis and Characterization of NiFe2O4 Nano-Octahedrons by EDTA-Assisted Hydrothermal Method

Nermin KASAPOĞLU, Abdulhadi BAYKAL, Muhammet S. TOPRAK

Catalytic Combustion of Ethyl Acetate

Tuğba Gürmen ÖZÇELİK, Süheyda ATALAY, Erden ALPAY