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Synthesis 2001(16): 2427-2430
DOI: 10.1055/s-2001-18721
DOI: 10.1055/s-2001-18721
PAPER
© Georg Thieme Verlag Stuttgart · New York
Synthesis and Properties of O-Vinylamidoximes
Further Information
Received
21 August 2001
Publication Date:
05 August 2004 (online)
Publication History
Publication Date:
05 August 2004 (online)
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Abstract
O-Vinylamidoximes 2 are synthesized from amidoximes 1 and acetylene in superbase systems (KOH/DMSO, KOH/NMP, NaOH/CsF/NMP) in a preparative yield of up to 80%. They decompose explosively above 150 °C, being resistant to solvolysis in the KOH/DMSO system (100 °C, 3 h) and to polymerization (AIBN, UV). Trifluoroacetylation of O-vinylbenzamidoxime 2b with (CF3CO)2O/pyridine gives 5-trifluoromethyl-3-phenyl-1,2,4-oxadiazole (3) in 49% yield.
Key words
O-vinylamidoximes - amidoximes - acetylene - heterocycle - superbase - vinylation - trifluoroacetylation
- 1
Trofimov BA.Mikhaleva AI. N-Vinylpyrroles Nauka; Novosibirsk:Katritzky AR. San Diego Press 1984. p.90-101 (in Russian) - 2
Trofimov BA. Adv. Heterocycl. Chem. 1990, 51: 280 - 3
Bean GP. In The Chemistry of Heterocyclic Compounds, Pyrroles Part 1, Vol. 48:Jones RA. Wiley; New York: 1990. p.153-155 - 4
Trofimov BA. In The Chemistry of Heterocyclic Compounds, Pyrroles Part 2, Vol. 48: Wiley; New York: 1992. p.131-298 - 5
Trofimov BA.Mikhaleva AI.Vasil’tsov AM.Schmidt EYu.Tarasova OA.Morozova LV.Sobenina LN.Preiss T.Henkelmann J. Synthesis 2000, 1125 - 6
Trofimov BA.Schmidt EYu.Mikhaleva AI.Vasil’tsov AM.Larina LI.Klyba LV. Mendeleev Commun. 1999, 238 - 7
Vasil’tsov AM.Schmidt EYu.Mikhaleva AI.Zaitsev AB.Tarasova OA.Afonin AV.Torjashinova D.-SD.Il′icheva LN .Trofimov BA. Russ. J. Org. Chem. 2001, 37: 334 - 8
Sohlberg K.Leary SP.Owen NL.Trofimov BA. Vibrational Spectroscopy 1997, 227 - 9
Afonin AV.Ushakov IA.Zinchenko SV.Tarasova OA.Trofimov BA. Magnetic Res. Chem. 2000, 38: 994 - 10
Heindel ND.Chun MC. Tetrahedron Lett. 1971, 1439 -
11a
Volkov AN.Sokolyanskaya LV.Trofimov BA. Izv. Akad. Nauk SSSR, Ser. Khim. 1976, 1430 - 12
Trofimov BA.Schmidt EYu.Mikhaleva AI.Vasil’tsov AM.Afonin AV. Mendeleev Commun. 2000, 29 - 13
Baram GI. J. Chrom. 1996, A 728: 387 - 14
Eloy F.Lenaers R. Chem. Rev. 1962, 62: 122 - 15
Witanovski M.Stefaniak L.Webb GA. In Annual Reports on NMR Spectroscopy Vol. 11B:Webb GA. Academic Press; London: 1981. p.502 - 16
Chemical Applications of Spectroscopy
West W. Interscience Publishers; New York: 1956.