Fe(II)/Et3N-Relay-catalyzed domino reaction of isoxazoles with imidazolium salts in the synthesis of methyl 4-imidazolylpyrrole-2-carboxylates, its ylide and betaine derivatives

Standard

Fe(II)/Et3N-Relay-catalyzed domino reaction of isoxazoles with imidazolium salts in the synthesis of methyl 4-imidazolylpyrrole-2-carboxylates, its ylide and betaine derivatives. / Galenko, E.E.; Tomashenko, O.A.; Khlebnikov, A.F.; Novikov, M.S.; Panikorovskii, T.L.

In: Beilstein Journal of Organic Chemistry, Vol. 11, 2015, p. 1732-1740.

Research output: Contribution to journal › Article › peer-review

BibTeX

@article{af3b6e2596a145e0931067d23d39b57c,

title = "Fe(II)/Et3N-Relay-catalyzed domino reaction of isoxazoles with imidazolium salts in the synthesis of methyl 4-imidazolylpyrrole-2-carboxylates, its ylide and betaine derivatives",

abstract = "{\textcopyright} 2015 Galenko et al; licensee Beilstein-Institut.A simple approach was developed for the synthesis of methyl 4-imidazolylpyrrole-2-carboxylates from easily available compounds, 5-methoxyisoxazoles and phenacylimidazolium salts under hybrid Fe(II)/Et3N relay catalysis. The products were easily transformed into the corresponding 3-(5-methoxycarbonyl-1H-imidazol-3-ium-3-yl)pyrrol-1-ides, which in turn can be hydrolyzed under basic conditions into the corresponding betaines. A carbene tautomeric form of the 4-methoxycarbonyl-substituted imidazolylpyrrolides was trapped by reaction with sulfur affording the corresponding imidazolethiones under very mild conditions.",

author = "E.E. Galenko and O.A. Tomashenko and A.F. Khlebnikov and M.S. Novikov and T.L. Panikorovskii",

year = "2015",

doi = "10.3762/bjoc.11.189",

language = "English",

volume = "11",

pages = "1732--1740",

journal = "Beilstein Journal of Organic Chemistry",

issn = "1860-5397",

publisher = "Beilstein-Institut Zur Forderung der Chemischen Wissenschaften",

}

RIS

TY - JOUR

T1 - Fe(II)/Et3N-Relay-catalyzed domino reaction of isoxazoles with imidazolium salts in the synthesis of methyl 4-imidazolylpyrrole-2-carboxylates, its ylide and betaine derivatives

AU - Galenko, E.E.

AU - Tomashenko, O.A.

AU - Khlebnikov, A.F.

AU - Novikov, M.S.

AU - Panikorovskii, T.L.

PY - 2015

Y1 - 2015

N2 - © 2015 Galenko et al; licensee Beilstein-Institut.A simple approach was developed for the synthesis of methyl 4-imidazolylpyrrole-2-carboxylates from easily available compounds, 5-methoxyisoxazoles and phenacylimidazolium salts under hybrid Fe(II)/Et3N relay catalysis. The products were easily transformed into the corresponding 3-(5-methoxycarbonyl-1H-imidazol-3-ium-3-yl)pyrrol-1-ides, which in turn can be hydrolyzed under basic conditions into the corresponding betaines. A carbene tautomeric form of the 4-methoxycarbonyl-substituted imidazolylpyrrolides was trapped by reaction with sulfur affording the corresponding imidazolethiones under very mild conditions.

AB - © 2015 Galenko et al; licensee Beilstein-Institut.A simple approach was developed for the synthesis of methyl 4-imidazolylpyrrole-2-carboxylates from easily available compounds, 5-methoxyisoxazoles and phenacylimidazolium salts under hybrid Fe(II)/Et3N relay catalysis. The products were easily transformed into the corresponding 3-(5-methoxycarbonyl-1H-imidazol-3-ium-3-yl)pyrrol-1-ides, which in turn can be hydrolyzed under basic conditions into the corresponding betaines. A carbene tautomeric form of the 4-methoxycarbonyl-substituted imidazolylpyrrolides was trapped by reaction with sulfur affording the corresponding imidazolethiones under very mild conditions.

U2 - 10.3762/bjoc.11.189

DO - 10.3762/bjoc.11.189

M3 - Article

VL - 11

SP - 1732

EP - 1740

JO - Beilstein Journal of Organic Chemistry

JF - Beilstein Journal of Organic Chemistry

SN - 1860-5397

ER -

ID: 3943769