RSS-Feed abonnieren
Bitte kopieren Sie die angezeigte URL und fügen sie dann in Ihren RSS-Reader ein.
https://www.thieme-connect.de/rss/thieme/de/10.1055-s-00000084.xml
Synthesis 2003(8): 1267-1271
DOI: 10.1055/s-2003-39410
DOI: 10.1055/s-2003-39410
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York
Zr(NO3)4: A Versatile Oxidizing Agent for Aromatization of Hantzsch 1,4-Dihydropyridines and 1,3,5-Trisubstituted Pyrazolines [1]
Weitere Informationen
Received
20 February 2003
Publikationsdatum:
26. Mai 2003 (online)
Publikationsverlauf
Publikationsdatum:
26. Mai 2003 (online)
Abstract
An efficient oxidative aromatization of Hantzsch 1,4-dihydropyridines and 1,3,5-trisubstituted pyrazolines to the corresponding pyridines and pyrazoles has been reported using Zr(NO3)4 in acetic acid at ambient temperature. The reactions are very fast and the products were isolated in high yields and in pure form.
Key words
1,4-dihydropyridines - pyrazolines - Zr(NO3)4 - aromatization
IICT Communication No. 030205.
-
2a
Janis RA.Triggle DJ. J. Med Chem. 1983, 25: 775 -
2b
Bocker RH.Guengerich FP. J. Med. Chem. 1986, 28: 1596 - 3
Wei XY.Rutledge A.Triggle DJ. J. Mol. Pharmacol. 1989, 35: 541 - For reviews, see for example:
-
4a
Godfraind T.Miller R.Wibo M. Pharmacol. Rev. 1986, 38: 321 -
4b
Janis RA.Silver PJ.Triggle DJ. Adv. Drug. Res. 1987, 16: 309 -
4c
Mager P.Coburn RA.Solo AJ.Triggle DJ.Rothe H. Drug Des. Discovery 1992, 8: 273 -
4d
Galian A. Drugs Future 1995, 20: 231 -
4e
Sannita WG.Busico S.Di Bon G.Ferrari A.Riela S. Int. J. Clin. Pharmacol. Res. 1993, 13: 281 - 5
Bocker RH.Guengerich FP. J. Med. Chem. 1986, 28: 1596 - 6
Khadikar B.Borkat S. Synth. Commun. 1998, 28: 207 ; and references cited therein -
7a
Kaneyama T, andNiwa H. inventors; (Takeda Chemical Industries, Ltd.); Japanese Patent 6806621. ; Chem. Abstr. 1968, 69, 106704 -
7b
Takabata E.Kodama R.Tanaka Y.Dohmori R.Tachizawa H.Naito T. Chem. Pharm. Bull. 1979, 16: 1900 -
7c
Polevoi LG. Tr. Nauchn. Konf. Aspiranotv I Ordinatorov [Pervyi] 1-yi Mosk. Med. Inst. Moscow 1964, 159 ; Chem. Abstr. 1966, 65: 19147 -
7d
Batulin YuM. Farmakol. Toksikol. 1968, 3: 533 ; Chem. Abstr. 1969, 70, 2236 -
7e
Parmar SS.Pandey BR.Dwivedi C.Harbison RD. J. Pharm. Sci. 1974, 63: 1152 -
7f
Soni N.Pande K.Kalsi R.Gupta TK.Parmer SS.Barthwal JP. Res. Commun. Chem. Pathol. Pharm. 1987, 56: 129 - 8
Balogh M.Hermecz I.Meszaros Z.Laszlo P. Helv. Chim. Acta 1984, 67: 2270 - 9
Pfister JR. Synthesis 1990, 689 - 10
Maquestion A.Mayence A.Eynde J.-JV. Tetrahedron Lett. 1991, 32: 3839 - 11
Eynde J.-JV.Mayence A.Maquestian A. Tetrahedron 1992, 48: 463 - 12
Boucher RH.Guengerich FD. J. Med. Chem. 1986, 29: 1596 - 13
Mashraqui SH.Karnik MA. Synthesis 1998, 713 - 14
Varma RS.Kumar D. Tetrahedron Lett. 1999, 40: 21 - 15
Anniyappan M.Muralidhran D.Perumal P.-T. Tetrahedron 2002, 58: 5069 - 16
Nakamichi N.Kawashita Y.Hayashi M. Org. Lett. 2002, 4: 3955 - 17
Yadav JS.Reddy BVS.Sabitha G.Reddy GSKK. Synthesis 2000, 1532 - 18
Gladstone WAF.Norman ROC. J. Chem Soc., Chem. Commun. 1966, 1536 - 19
Bhatnagar I.George MV. Tetrahedron 1968, 24: 1293 - 20
Smith LI.Howard KL. J. Am. Chem. Soc. 1943, 65: 159 - 21
Singh SP.Kumar D.Prakash O.Kapoor RP. Synth. Commun. 1997, 27: 2683 - 22
Dodwadmath RP.Wheeler TS. Proc. Ind. Acad. Sci. 1935, 2A: 438 ; Chem. Abstr. 1936, 30, 1770 - 23
Loey B.Snader KM. J. Org. Chem. 1965, 30: 1914 - 24
Cook AH.Heilbron IM.Steger L. J. Chem. Soc. 1943, 413 - 25
Engelman F. Liebigs Ann. Chem. 1885, 231: 37 - 26
Memarian HR.Sadeghi MM.Momeni AR. Indian J. Chem. 1999, 38B: 800 - 27
Harris DJ.Kan GYP.Snieckus V. Can. J. Chem. 1974, 52: 2798 - 28
Foote RS.Beam CF.Hauser CR. J. Heterocycl. Chem. 1970, 7: 589
References
IICT Communication No. 030205.