Selective syntheses of 2H-1,3-oxazines and 1H-pyrrol-3(2H)-ones via temperature-dependent Rh(II)-carbenoid-mediated 2H-azirine-ring expansion

Tetrahedron - Tập 70 - Trang 3377-3384 - 2014
Kirill V. Zavyalov1, Mikail S. Novikov1, Alexander F. Khlebnikov1, Viktoriia V. Pakalnis1
1Institute of Chemistry, Saint-Petersburg State University, Universitetskii Pr. 26, 198504 St. Petersburg, Russia

Tài liệu tham khảo

Khlebnikov, 2013, Tetrahedron, 69, 3363, 10.1016/j.tet.2013.02.020 Rostovskii, 2013, Org. Biomol. Chem., 11, 5535, 10.1039/c3ob40708j Alves, 2011, 145 Padwa, 2010, Adv. Heterocycl. Chem., 99, 1, 10.1016/S0065-2725(10)09901-0 Lemos, 2009, Molecules, 14, 4098, 10.3390/molecules14104098 Pinho e Melo, 2004, Curr. Org. Synth., 1, 275, 10.2174/1570179043366729 Palacios, 2001, Eur. J. Org. Chem., 2401, 10.1002/1099-0690(200107)2001:13<2401::AID-EJOC2401>3.0.CO;2-U Novikov, 2012, Tetrahedron Lett., 53, 5777, 10.1016/j.tetlet.2012.08.063 Khlebnikov, 2006, Russ. J. Org. Chem., 42, 533, 10.1134/S1070428006040075 Khlebnikov, 2004, Tetrahedron Lett., 45, 6003, 10.1016/j.tetlet.2004.06.038 Khlebnikov, 2006, Russ. J. Org. Chem., 42, 515, 10.1134/S1070428006040075 Rostovskii, 2013, Tetrahedron, 69, 4292, 10.1016/j.tet.2013.03.106 Khlebnikov, 2009, Tetrahedron Lett., 50, 6509, 10.1016/j.tetlet.2009.09.033 Zavyalov, 2013, Tetrahedron, 69, 4546, 10.1016/j.tet.2013.04.022 Barluenga, 1996, Tetrahedron, 52, 3095, 10.1016/0040-4020(95)01097-1 Francois-Endelmond, 2010, Org. Lett., 12, 40, 10.1021/ol9024309 Barluenga, 1993, J. Chem. Soc., Chem. Commun., 217, 10.1039/C39930000217 Schmidt, 1970, Chem. Ber., 103, 2760, 10.1002/cber.19701030907 Manning, 2008, J. Am. Chem. Soc., 130, 8602, 10.1021/ja803139k Manning, 2008, Tetrahedron, 64, 6901, 10.1016/j.tet.2008.03.010 Kashima, 1980, J. Chem. Soc., Perkin Trans. 1, 1866, 10.1039/p19800001866 Padwa, 1975, J. Am. Chem. Soc., 97, 4682, 10.1021/ja00849a034 Singh, 1972, J. Am. Chem. Soc., 94, 1199, 10.1021/ja00759a028 Maeda, 1977, J. Chem. Soc., Perkin Trans. 1, 239, 10.1039/p19770000239 Zen, 1982, Chem. Lett., 1711, 10.1246/cl.1982.1711 Brahma, 2008, J. Heterocycl. Chem., 45, 311, 10.1002/jhet.5570450203 Bàtori, 1994, Tetrahedron, 50, 4699, 10.1016/S0040-4020(01)85009-2 Brahma, 2005, Tetrahedron Lett., 46, 6575, 10.1016/j.tetlet.2005.07.086 Wasserman, 1993, Heterocycles, 35, 975, 10.3987/COM-92-S(T)92 Momose, 1978, Chem. Pharm. Bull., 26, 3521, 10.1248/cpb.26.3521 Momose, 1977, Heterocycles, 6, 1827, 10.3987/R-1977-11-1827 Campaigne, 1974, J. Heterocycl. Chem., 11, 929, 10.1002/jhet.5570110614 Hill, 2009, Synthesis, 2531 Chong, 1967, Aust. J. Chem., 20, 935, 10.1071/CH9670935 Momose, 1978, Chem. Pharm. Bull., 26, 2224, 10.1248/cpb.26.2224 Gordon, 1984, J. Chem. Soc., Perkin Trans. 1, 2129, 10.1039/p19840002129 Briehl, 1984, J. Org. Chem., 49, 2772, 10.1021/jo00189a025 Gordon, 1983, J. Chem. Soc., Chem. Commun., 957, 10.1039/c39830000957 Schiess, 1972, Angew. Chem., Int. Ed. Engl., 11, 288, 10.1002/anie.197202881 Smit, 1975, J. Chem. Soc., Chem. Commun., 513, 10.1039/C39750000513 Paton, 2011, J. Am. Chem. Soc., 133, 3895, 10.1021/ja107988b Sakaguchi, 2011, Org. Lett., 13, 4292, 10.1021/ol2016302 Zhao, 2004, J. Phys. Chem. A, 108, 6908, 10.1021/jp048147q Grigg, 1987, Chem. Soc. Rev., 16, 89, 10.1039/cs9871600089 Mancebo-Aracil, 2012, ChemPlusChem, 77, 770, 10.1002/cplu.201200107 Bazureau, 1993, Tetrahedron Lett., 34, 4639, 10.1016/S0040-4039(00)60644-5 Bazureau, 2001, Tetrahedron Lett., 42, 6097, 10.1016/S0040-4039(01)01190-X Crovetto, 2008, Synlett, 1840 Chen, 2010, Chem. Commun., 1275 Li, 2009, Org. Lett., 11, 2643, 10.1021/ol9006663 Goddard-Borger, 2007, Org. Lett., 9, 3797, 10.1021/ol701581g Shi, 1990, J. Org. Chem., 55, 3383, 10.1021/jo00297a075 Frisch, 2010