Czasopismo
Tytuł artykułu
Autorzy
Warianty tytułu
Języki publikacji
Abstrakty
A general one-pot synthesis of dibenz[b,f][1,4] oxazepine-11(10H)-carboxamides is described. The Ugi four-component reaction (U-4CR) of 2-aminophenols, cyclohexyl isocyanide, 2-chloro-5-nitrobenzaldehyde, and 2-bromobenzoic acids in MeOH in the presence of 25 mol% Mg(ClO4)2 at 30-40 .C for 22-95 h gave the linear Ugi products. The latter were treated with aqueous K2CO3 in MeOH under microwave heating at 120 .C for 10 min for promoting the intramolecular nucleophilic aromatic substitution (SNAr), affording the 6/7/6-fused tricyclic heterocycles in 61-85% yields.
Czasopismo
Rocznik
Tom
Numer
Opis fizyczny
Daty
otrzymano
2014-05-17
zaakceptowano
2014-06-20
online
2014-07-08
Twórcy
autor
- Laboratory of Asymmetric Catalysis and Synthesis, Department of Chemistry, Zhejiang University, Hangzhou 310027, P. R. of China
autor
- Laboratory of Asymmetric Catalysis and Synthesis, Department of Chemistry, Zhejiang University, Hangzhou 310027, P. R. of China
autor
- Laboratory of Asymmetric Catalysis and Synthesis, Department of Chemistry, Zhejiang University, Hangzhou 310027, P. R. of China
Bibliografia
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- [4] (a) El Kaïm, L.; Grimaud, L. Tetrahedron 2009, 65, 2153-2171. (b) van der Heijden, G.; Ruijter, E.; Orru, R. V. A. Synlett 2013, 24, 666-685.
- [5] Akritopoulou-Zanze, I.; Djuric, S. W. Heterocycles 2007, 73, 125-147.
- [6] (a) Sunderhaus, J. D.; Martin, S. F. Chem. Eur. J. 2009, 15, 1300-1308. (b) Banfi, L.; Riva, R.; Basso, A. Synlett 2010, 23-41. (c) Koopmanschap, G.; Ruijter, E.; Orru, R. V. A. Beilstein J. Org. Chem. 2014, 10, 544-598.
- [7] Dai, W.-M. Diversity Oriented Synthesis 2012, 1, 11-20.
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- [12] Anstas, P. T.; Warner, J. C. Green Chemistry: Theory and Practice; Oxford University Press: New York, 1998.
- [13] Xing, X.; Wu, J.; Feng, G.; Dai, W.-M. Tetrahedron 2006, 62, 6774-6781.
- [14] Feng, G.; Wu, J.; Dai, W.-M. Tetrahedron Lett. 2007, 28, 401-404.
- [15] Xing, X.; Wu, J.; Luo, J.; Dai, W.-M. Synlett 2006, 2099-2103.
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- [21] Ma, Y.; Qian, C.; Xie, M.; Sun, J. J. Org. Chem. 1999, 64, 6462-6467.
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Typ dokumentu
Bibliografia
Identyfikatory
Identyfikator YADDA
bwmeta1.element.-psjd-doi-10_2478_dos-2014-0001