Synthesis of 1,2,4-triazole C-nucleosides from hydrazonyl chlorides and nitriles

Nucleosides, Nucleotides and Nucleic Acids

Volumn 26, Issue 1, 2007, Pages 37-43

  Al Masoudi, Najim A ^a   Al Soud, Yaseen A ^b   Ali, Ibrahim A I ^c  

^a UNIVERSITY OF KONSTANZ   (Germany)

^b AL AL BAYT UNIVERSITY   (Jordan)

^c Suez Canal University   (Egypt)

Author keywords

1,2,4 triazoles; C nucleosides; Hydrazonyl chlorides; Pharmacological activity

Indexed keywords

CHLORIDE; CYANIDE; HYDRAZINE DERIVATIVE; HYDRAZONE DERIVATIVE; NITRILE; NUCLEOSIDE DERIVATIVE; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE; RIBOSE; SILVER NITRATE; TRIAZOLE DERIVATIVE; YTTERBIUM;

ARTICLE; CATALYSIS; CONFORMATION; CYCLIZATION; MASS SPECTROMETRY; NUCLEAR OVERHAUSER EFFECT; PROTON NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; SYNTHESIS;

ANTIVIRAL AGENTS; CHLORIDES; HYDRAZONES; MESYLATES; NITRILES; ORGANOMETALLIC COMPOUNDS; RIBONUCLEOSIDES; SILVER NITRATE; TRIAZOLES;

EID: 33845681451     PISSN: 15257770     EISSN: 15322335     Source Type: Journal    
DOI: 10.1080/15257770601052265     Document Type: Article

References (24)

1. Naito, Y.; Akahoshi, F.; Takeda, S.; Takada, T.; Kajii, M.; Nishimura, H.; Sugiura, M.; Fukaya, C.; Kagitani, Y. Synthesis and pharmacological activity of triazole derivatives inhibiting eosinophilia. J. Med. Chem. 1996, 39, 3019-3029.
2. De Clercq, E. Antiviral drugs in current clinical use. J. Clin. Virol. 2004, 30, 115-133.
3. Collin, X.; Sauleau, A.; Coulon, J. 1,2,4-Triazolo mercapto and aminonitriles as potent antifungal agents. Bioorg. Med. Chem. Lett. 2003, 13, 2601-2605.
4. Sui, Z.; Guan, J.; Hlasta, D.J.; Macielag, M.J.; Foleno, B.D.; Goldschmidt, R.M.; Loeloff, M.J.; Webb, G.C.; Barrett, J.F. SAR studies of diaryltriazoles against bacterial two-component regulatory systems and their antibacterial activities. Bioorg. Med. Chem. Lett. 1998, 8, 1929-1934.
5. Hester, J.B.; Rudzik, A.D.; Kamdar, B.V. 6-Phenyl-4H-s-triazolo[4,3- α][1,4]benzo-diazepines which have central nervous system depressant activity. J. Med. Chem. 1971, 14, 1078-1081.
6. Heubach, G.; Sachse, B.; Buersteu, H. 1,2,4-Triazol derivatives. Ger. Offen. Pat. 2826760, Chem. Abstr. 1980, 92, 181200h.
7. Tanaka, G. Pesticidal triazolyl diphatic sulfonates. Japan Kokai, 74 95973, Chem. Abstr. 1975, 82, 156320h.
8. Goss, P.E.; Strasser-Weippl, K. Aromatase inhibitors for chemoprevention. Best Pract. Res. Clin. End. Met. 2004, 18, 113-130.
9. Santen, J.R. Inhibition of aromatase: insights from recent studies. Steroids 2003, 68, 559-567.
10. Clemons, M.; Coleman, R.E.; Verma, S. Aromatase inhibitors in the adjuvant setting: bringing the gold to a standard? Cancer Treat. Rev. 2004, 30, 325-332.
11. Al-Masoudi, N.A.; Hassan, N.A.; Al-Soud, Y.A.; Schmidt, P.; Gaafer, A.E.-D.M.; Weng, M.; Marino, S.; Schoch, A.; Amer, A.; Jochims, J.C. Synthesis of C- and N-nucleosides from 1-aza-2-azoniaellene and 1,3-diaza-2-azoniaaallene salts. Chem. Soc. Perkin Trans. 1 1998,, 947-953.
12. Al-Soud, Y.A.; Al-Masoudi, W.A.; El-Halawa, R.A.; Al-Masoudi, N.A. Synthesis and antiviral activity of some 1,2,4-triazole C-nucleosides from 1-(chloroalkyl)-1-aza-2-azo-niaallene salts. Nucleosides Nucleotides 1999, 18, 1985-1994.
13. Al-Masoudi, I.A.; Al-Soud, Y.A.; Al-Salihi, N.J.; Al-Masoudi, N.A. 1,2,4-Triazoles: Synthetic approaches and pharmacological importance. Chem. Heterocycl. Compd. 2006, 11, 1605-1634.
14. Moon, M.W. Chlorination of aldehyde and ketone phenylhydrazones. J. Org. Chem. 1972, 37, 383-385.
15. Wang, Q.; Jochims, J.C.; Köhlbrandt, S.; Dahlenburg, L.; Al-Talib, M.; Hamed, A.; Ismail, E.A. 1,2,4-Triazolium salts from the reaction of 1-aza-2-azaiaaallene salts with nitrile. Synthesis 1992, 710-718.
16. Al-Soud, Y.A.; Qalalweh, N.A.; Al-Sa'adoni, H.H.; Al-Masoudi, N.A. New benzyl-piperazine derivatives bearing mono and bis-dialkyl-substituted 1,2,4-triazoles. Heteroatom Chem. 2005, 16, 28-32, references therein.
17. Hegarty, A.F.; Kearney, J.A. Substituent effects on the solvolysis of α,β′-dichloroazoalkanes. Evidence for open aza-allylic ion intermediates on reaction pathway. J. Org. Chem. 1975, 40, 3529-3536, references therein.
18. Su, W.; Yang, D.; Li, J. Novel process for synthesis of 1,2,4-triazoles: Ytterbium triflate-catalyzed cyclization of hydrazonyl chlorides with nitriles. Synth. Commun. 2005, 35, 1435-1440.
19. 3. Tetrahedron 2000, 56, 8071-8076.
20. Buzykin, B.I.; Bredikhina, Z.A. An approach to 1-aryl-1,2,4-triazoles. Synthesis 1993, 59-61.
21. Bothner-By, A.A.; Stephensen, R.L.; Lee, J.; Warren, C.D.; Jeanloz, R.W. Structure determination of a tetrasaccharide: transient nuclear Overhauser effects in the rotating frame. J. Am. Chem. Soc. 1984, 106, 811-813.
22. Wolfrom, M.L.; Thompson, A. The reactive form of glucose oxime. J. Am. Chem. Soc. 1931, 53, 622-632.
23. Gautun, O.R.; Carlsen, P.H.J. Regioselectivity in the thermal rearrangement of unsymmetrical 4-methyl-4H-1,2,4-triazoles to 1-methyl-1H-1,2,4-triazoles. Moecules 2001, 6, 969-978.
24. Al-Masoudi, N.A.; Al-Soud, Y.A.; Al-Masoudi, I.A. Thiopyridone nucleosides: Synthesis, antibacterial and antiviral activity of 7-(glycoyl and D-manno-hextitol-1-yl)-2-chloro-4-oxothieno[2,3-a]pyridine-5-carboxylic acids. Sulfur Lett. 2000, 24, 13-22.