Preparation of imidazolines from aziridines and nitriles via TfOH promoted Ritter process
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关键词:
- Ritter reaction
- / Nitrile
- / TfOH
- / Aziridine
- / Imidazoline
English
Preparation of imidazolines from aziridines and nitriles via TfOH promoted Ritter process
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Key words:
- Ritter reaction
- / Nitrile
- / TfOH
- / Aziridine
- / Imidazoline
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[3] (a) P.I. Dalko, Y. Langlois, Stereoselective preparation of quaternary benzylic centres using chiral imidazolines, Chem. Commun. (1998) 331-332; (b) T. Morimoto, K. Tachibana, K. Achiwa, ChemInform abstract: asymmetric reactions catalyzed by chiral metal complexes. Part 78. Chiral thioimidazoline ligands for palladium-catalyzed asymmetric allylation, Synlett 28 (1997) 783-785.[3] (a) P.I. Dalko, Y. Langlois, Stereoselective preparation of quaternary benzylic centres using chiral imidazolines, Chem. Commun. (1998) 331-332; (b) T. Morimoto, K. Tachibana, K. Achiwa, ChemInform abstract: asymmetric reactions catalyzed by chiral metal complexes. Part 78. Chiral thioimidazoline ligands for palladium-catalyzed asymmetric allylation, Synlett 28 (1997) 783-785.
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[4] (a) J.J. Ritter, P.P. Minieri, A new reaction of nitriles. I. Amides from alkenes and mononitriles, J. Am. Chem. Soc. 70 (1948) 4045-4048; (b) J.J. Ritter, J. Kalish, A new reaction of nitriles. Ⅱ. Synthesis of t-carbinamines, J. Am. Chem. Soc. 70 (1948) 4048-4050.[4] (a) J.J. Ritter, P.P. Minieri, A new reaction of nitriles. I. Amides from alkenes and mononitriles, J. Am. Chem. Soc. 70 (1948) 4045-4048; (b) J.J. Ritter, J. Kalish, A new reaction of nitriles. Ⅱ. Synthesis of t-carbinamines, J. Am. Chem. Soc. 70 (1948) 4048-4050.
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[5] (a) M.Y. Lebedev, M.B. Erman, Lower primary alkanols and their esters in a Rittertype reaction with nitriles. An efficient method for obtaining N-primary-alkyl amides, Tetrahedron Lett. 43 (2002) 1397-1399; (b) M. Dos Santos, B. Crousse, D. Bonnet-Delpon, Improved Ritter reaction with CF3-containing oxirane for an access to central units of protease inhibitors, Tetrahedron Lett. 50 (2009) 857-859; (c) P. Rubenbauer, T. Bach, Diastereoselective Ritter reactions of chiral secondary benzylic alcohols, Chem. Commun. (2009) 2130-2132.[5] (a) M.Y. Lebedev, M.B. Erman, Lower primary alkanols and their esters in a Rittertype reaction with nitriles. An efficient method for obtaining N-primary-alkyl amides, Tetrahedron Lett. 43 (2002) 1397-1399; (b) M. Dos Santos, B. Crousse, D. Bonnet-Delpon, Improved Ritter reaction with CF3-containing oxirane for an access to central units of protease inhibitors, Tetrahedron Lett. 50 (2009) 857-859; (c) P. Rubenbauer, T. Bach, Diastereoselective Ritter reactions of chiral secondary benzylic alcohols, Chem. Commun. (2009) 2130-2132.
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[6] R.M.A. Pinto, J.A.R. Salvador, C. Le Roux, Ritter reaction mediated by bismuth(ⅡI) salts: one-step conversion of epoxides into vic-acylamino-hydroxy compounds, Synlett (2006) 2047-2050.[6] R.M.A. Pinto, J.A.R. Salvador, C. Le Roux, Ritter reaction mediated by bismuth(ⅡI) salts: one-step conversion of epoxides into vic-acylamino-hydroxy compounds, Synlett (2006) 2047-2050.
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[7] (a) T. Hiyama, H. Koide, S. Fujita, H. Nozaki, Reaction of N-alkoxycarbonylaziridines with nitriles, Tetrahedron 29 (1973) 3137-3139; (b) B.A.B.Prasad,G.Pandey,V.K.Singh,Synthesisofsubstitutedimidazolinesvia[3 + 2]- cycloaddition of aziridineswith nitriles, Tetrahedron Lett. 45 (2004) 1137-1141; (c) V.K. Yadav, V. Sriramurthy, Silylmethyl-substituted aziridine and azetidine as masked 1,3- and 1,4-dipoles for formal [3 + 2] and [4 + 2] cycloaddition reactions, J. Am. Chem. Soc. 127 (2005) 16366-16367; (d) M.K.Ghorai,K.Das,A.Kumar,K.Ghosh,Anefficientroutetoregioselectiveopeningof N-tosylaziridineswith zinc(Ⅱ) halides, Tetrahedron Lett. 46 (2005) 4103-4106; (e) J.Wu,X.Y.Sun,H.G.Xia,Sc(OTf)3-catalyzed[3 + 2]-cycloadditionofaziridineswith nitriles under solvent-free conditions, Tetrahedron Lett. 47 (2006) 1509-1512; (f) M.K.Ghorai,K.Ghosh,K.Das,Copper(Ⅱ)triflatepromotedcycloadditionofa-alkylor aryl substituted N-tosylaziridines with nitriles: a highly efficient synthesis of substituted imidazolines, Tetrahedron Lett. 47 (2006) 5399-5403; (g) S.Gandhi,A.Bisai,B.A.B.Prasad,V.K.Singh,Studiesonthereactionofaziridineswith nitriles and carbonyls: synthesis of imidazolines and oxazolidines, J. Org. Chem. 72 (2007) 2133-2142.[7] (a) T. Hiyama, H. Koide, S. Fujita, H. Nozaki, Reaction of N-alkoxycarbonylaziridines with nitriles, Tetrahedron 29 (1973) 3137-3139; (b) B.A.B.Prasad,G.Pandey,V.K.Singh,Synthesisofsubstitutedimidazolinesvia[3 + 2]- cycloaddition of aziridineswith nitriles, Tetrahedron Lett. 45 (2004) 1137-1141; (c) V.K. Yadav, V. Sriramurthy, Silylmethyl-substituted aziridine and azetidine as masked 1,3- and 1,4-dipoles for formal [3 + 2] and [4 + 2] cycloaddition reactions, J. Am. Chem. Soc. 127 (2005) 16366-16367; (d) M.K.Ghorai,K.Das,A.Kumar,K.Ghosh,Anefficientroutetoregioselectiveopeningof N-tosylaziridineswith zinc(Ⅱ) halides, Tetrahedron Lett. 46 (2005) 4103-4106; (e) J.Wu,X.Y.Sun,H.G.Xia,Sc(OTf)3-catalyzed[3 + 2]-cycloadditionofaziridineswith nitriles under solvent-free conditions, Tetrahedron Lett. 47 (2006) 1509-1512; (f) M.K.Ghorai,K.Ghosh,K.Das,Copper(Ⅱ)triflatepromotedcycloadditionofa-alkylor aryl substituted N-tosylaziridines with nitriles: a highly efficient synthesis of substituted imidazolines, Tetrahedron Lett. 47 (2006) 5399-5403; (g) S.Gandhi,A.Bisai,B.A.B.Prasad,V.K.Singh,Studiesonthereactionofaziridineswith nitriles and carbonyls: synthesis of imidazolines and oxazolidines, J. Org. Chem. 72 (2007) 2133-2142.
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[8] K.I. Booker-Milburn, D.J. Guly, B. Cox, P.A. Procopiou, Ritter-type reactions of Nchlorosaccharin: a method for the electrophilic diamination of alkenes, Org. Lett. 5 (2003) 3313-3315.[8] K.I. Booker-Milburn, D.J. Guly, B. Cox, P.A. Procopiou, Ritter-type reactions of Nchlorosaccharin: a method for the electrophilic diamination of alkenes, Org. Lett. 5 (2003) 3313-3315.
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