The ene-like reaction of naphtalen-1-ylamine and naphtalen-2-ylamine, and pyridin-2-ylamine with diethyl azodicarboxylate (DEAD) as well as that of naphthalen-2-ol with 4-phenyl-1,2,4-trizoline-3,5-dione is catalyzed by lithium perchlorate. Also conversion of ester function of (DEAD) to amide function in reaction with 2-aminopyridine and further rearrangement of ethyl N-pyridyn-2-ylcarbamoylazoformate into ethyl pyridin-2-ylcarbamate are catalyzed by LiClO4.
Similar content being viewed by others
References
O. Diels J. Back (1921) Chem. Ber. 54 213
R. Huisgen, F. Jakob, W. Siegel, A. Cadus, Liebigs. (1969). Ann. Chem. 590 (1954) 1; R.R.B. Carlin, M.S. Moores, J. Am. Chem. Soc. 84 (1962) 4107; S.H. Schroeter, J. Org. Chem. 34 (1969) 4012
R. Lenarsic M. Kocevar S. Polanc (1999) J. Org. Chem. 64 2558 Occurrence Handle10.1021/jo9821170
W.J. Kinart, C.M. Kinart, J. Organomet. Chem. 665 (2003) 233; W.J. Kinart, C.M. Kinart, Q.T. Tran, R. Oszczeda, Main Group Met. Chem. 27 (2004) 241
W.J. Kinart C.M. Kinart Q.T. Tran R. Oszczeda R. Nazarski (2004) Appl. Organomet. Chem. 18 398 Occurrence Handle10.1002/aoc.681
A.G. Davies, W.J. Kinart, J. Chem. Soc. Perkin Trans. 2 (1993) 2281; W.J. Kinart, J. Chem. Res.(S) (1999) 46; W.J. Kinart, E. Sniec, I. Tylak, C.M. Kinart, Phys. Chem. Liquids 38 (2000) 193; W.J. Kinart, C.M. Kinart, I. Tylak, J. Organomet. Chem. 608 (2000) 49; W.J. Kinart, C.M. Kinart, I. Tylak, K. Mikolajczak, Phys. Chem. Liquids 40 (2002) 405; W.J. Kinart, C.M. Kinart, Phys. Chem. Liquids 42 (2003) 173; W.J. Kinart, R. Nazarski, C.M. Kinart, Q.T. Tran and R. Oszczeda, Synth. Commun. 35 (2005) 1059
I. Zaltsgendler Y. Leblanc M.A. Berstein (1993) Tetrahedron Lett. 34 2441 Occurrence Handle10.1016/S0040-4039(00)60436-7
C. Dufresne Y. Leblanc C. Berthelette C. McCooeye (1997) Synth. Commun. 27 3613
J.P. Demers D.H. Klaubert (1987) Tetrahedron Lett. 28 4933 Occurrence Handle10.1016/S0040-4039(00)96662-0
U. Rangarsson (2005) Chem. Soc. Rev. 30 205 Occurrence Handle10.1039/b010091a
O. Tsubrik U. Maeorg U. Rangarsson (2002) Tetrahedron Lett. 43 6213 Occurrence Handle10.1016/S0040-4039(02)01327-8
L. Grehn, H. Lonn and U. Rangarsson, Chem. Commun. (1997) 1381
H. Han K.D. Janda (1996) J. Am. Chem. Soc. 118 2539 Occurrence Handle10.1021/ja9535470
A. Cheguillaume F. Lehardy K. Bouget M. Baudy-Floc’h P.L. Grei (1999) J. Org. Chem. 64 2924 Occurrence Handle10.1021/jo981487l Occurrence Handle11674368
C.I. Gray, M. Quibell, K.-L. Jiang and N.Bagget, Synhesis (1991) 141
J.S. Nowick M. Parish I.Q. Lee D.L. Holmes J.W. Ziller (1997) J. Am. Chem. Soc. 119 5413 Occurrence Handle10.1021/ja963843s
R. Thiericke A. Zeek (1998) J. Chem. Soc. Perkin Trans. 1 2123
S. Hernandez R. San Martin I. Tellitu E. Dominguez (2003) Org. Lett. 5 1095 Occurrence Handle10.1021/ol034148+ Occurrence Handle12659582
S.R. Stauffer Y.R. Haung Z.D. Aron C.J. Coletta J. Sun B.S. Katzenellenbogen (2001) Bioorg. Med. Chem. 9 151 Occurrence Handle10.1016/S0968-0896(00)00226-1 Occurrence Handle11197335
N. Boudreault Y. Leblanc (1996) Synthese 74 241
S. Bozzini P. Nitti G. Pitacco A. Pizzioli C.J. Russo (1996) Heterocycl. Chem. 33 1217
B. Wunsh, S. Nerdinger and G. Hofner, Liebigs Ann. (1995) 1303
J.B. Arterburn K.V. Rao R.B. Ramadas R. Dible (2001) Org. Lett. 3 1351 Occurrence Handle10.1021/ol015731y Occurrence Handle11348232
S. Bombek, R. Lenarsic, M. Kocevar, L. Saint-Jalmes, J.R. Desmurs and S. Polanc, Chem. Commun. (2002) 1494
J.S. Yadow, B.V.S. Reddy, G. Veerendhar, R.S. Rao, K.Nagaiah, Chem. Lett. (2002) 318
J.S. Yadow, B.V.S. Reddy, G.M. Kumar, C. Madan, Synlett. (2001) 1781
Y. Leblanc N.J. Boudreault (1995) J. Org. Chem. 60 4268 Occurrence Handle10.1021/jo00118a052
H. Mitchel Y. Leblanc (1994) J. Org. Chem. 59 682 Occurrence Handle10.1021/jo00082a035
G.W. Kobalka S.K. Guchhait (2003) Org. Lett. 5 4129 Occurrence Handle10.1021/ol035544v Occurrence Handle14572266
L. Bauer, O. Exner, Angew. Chem. Int. Ed. Eng. 13 (1974) 376; H.L. Yale, Chem. Rev. 33 (1943) 209
H.H. Szmant (1968) Angew. Chem. Int. Ed. Eng. 7 120 Occurrence Handle10.1002/anie.196801201
U. Luning, C. Kuhl and A. Uphoff, Eur. J. Org. Chem. (2002) 4063
A.R. Katritzky, J. Chem. Soc. (1956) 2063
E.J. Moriconi R.E. Misner (1969) J. Org. Chem. 34 5072
R.M. Wilson N. Chantarasiri (1982) J. Am. Chem. Soc. 104 555 Occurrence Handle10.1021/ja00366a031
R. Alberto R. Schibli A.P. Schubiger U. Abram H.-J. Pitzsch B. Johannsen (1999) J. Am. Chem. Soc. 121 6076 Occurrence Handle10.1021/ja990765a
D.S. Edwards S. Liu A.R. Harris M.J. Poirier B.A. Ewels (1999) Bioconjugate Chem. 10 803 Occurrence Handle10.1021/bc990022e
D.J. Rose K.P. Maresca T. Nicholson A. Davison A.G. Jones J. Babich A. Fischman W. Graham J.R.D. DeBord J. Zubieta (1998) Inorg. Chem. 37 2701 Occurrence Handle10.1021/ic970352f Occurrence Handle11670406
Author information
Authors and Affiliations
Corresponding author
Rights and permissions
About this article
Cite this article
Kinart, W.J., Kinart, C.M., Oszczeda, R. et al. Studies on the Catalysis by Lithium Perchlorate of Reactions of Aromatic Amines with Diethyl Azodicarboxylate and Naphtalen-2-ol with 4-phenyl-1,2,4-triazoline-3,5-dione. Catal Lett 103, 185–189 (2005). https://doi.org/10.1007/s10562-005-7152-8
Received:
Accepted:
Issue Date:
DOI: https://doi.org/10.1007/s10562-005-7152-8