Novel synthesis of 4(5)-monosubstituted imidazoles via cycloaddition of tosylmethyl isocyanide to aldimines

Tetrahedron

Volumn 53, Issue 33, 1997, Pages 11355-11368

  Ten Have, Ronald ^a   Huisman, Marco ^a   Meetsma, Auke ^a   Van Leusen, Albert M ^a  

^a UNIVERSITY OF GRONINGEN   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; ALDIMINE DERIVATIVE; IMIDAZOLE DERIVATIVE; N (DIMETHYLSULFAMOYL)ALDIMINE; N (DIMETHYLSULFAMOYL)IMIDAZOLE; N TOSYLALDIMINE; TOSYLMETHYLISOCYANIDE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CONTROLLED STUDY; CYCLIZATION; DRUG SYNTHESIS; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; TECHNIQUE;

EID: 0030749151     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00717-5     Document Type: Article

References (47)

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37. For the sake of completeness, it should be mentioned that in two related reactions of (isocyanotosylmethylidene)cyclohexane (instead of TosMIC) with N-tosylaldimines in non-protic solvents trisubstituted imidazoles were obtained, in which the N-tosyl group was retained in the product. See, Moskal, J.; van Stralen, R.; Postma, D., van Leusen, A.M. Tetrahedron Lett. 1986, 27, 2173, and Leusink, F.R., Ph. D. Thesis, Groningen University, 1993, p. 85-97.
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44. Programs : Beurskens, P.T.; Beurskens, G.; Bosman, W.P.; de Gelder, R.; Garcia-Granda, S.; Coul, R.O.; Israel, R.; Smits, J.M.M. DIRDIFF-96, 1996, Crystallography Laboratory, University of Nijmegen, The Netherlands; least-square refinements : Sheldrick, G.M. SHELXL93, Program for the Refinement of Crystal Structures, 1993, University of Göttingen, Germany; calculation of geometric data : Spek, A.L. Platon, Program for the Automated Analysis of Molecular Geometry, 1996, University of Utrecht, The Netherlands; preparation of illustrations : Meetsma, A. PLUTO, Program for Display and Analysis of Crystal and Molecular Structures, 1996, University of Groningen, The Netherlands.
45. Programs : Beurskens, P.T.; Beurskens, G.; Bosman, W.P.; de Gelder, R.; Garcia-Granda, S.; Coul, R.O.; Israel, R.; Smits, J.M.M. DIRDIFF-96, 1996, Crystallography Laboratory, University of Nijmegen, The Netherlands; least-square refinements : Sheldrick, G.M. SHELXL93, Program for the Refinement of Crystal Structures, 1993, University of Göttingen, Germany; calculation of geometric data : Spek, A.L. Platon, Program for the Automated Analysis of Molecular Geometry, 1996, University of Utrecht, The Netherlands; preparation of illustrations : Meetsma, A. PLUTO, Program for Display and Analysis of Crystal and Molecular Structures, 1996, University of Groningen, The Netherlands.
46. Programs : Beurskens, P.T.; Beurskens, G.; Bosman, W.P.; de Gelder, R.; Garcia-Granda, S.; Coul, R.O.; Israel, R.; Smits, J.M.M. DIRDIFF-96, 1996, Crystallography Laboratory, University of Nijmegen, The Netherlands; least-square refinements : Sheldrick, G.M. SHELXL93, Program for the Refinement of Crystal Structures, 1993, University of Göttingen, Germany; calculation of geometric data : Spek, A.L. Platon, Program for the Automated Analysis of Molecular Geometry, 1996, University of Utrecht, The Netherlands; preparation of illustrations : Meetsma, A. PLUTO, Program for Display and Analysis of Crystal and Molecular Structures, 1996, University of Groningen, The Netherlands.
47. Programs : Beurskens, P.T.; Beurskens, G.; Bosman, W.P.; de Gelder, R.; Garcia-Granda, S.; Coul, R.O.; Israel, R.; Smits, J.M.M. DIRDIFF-96, 1996, Crystallography Laboratory, University of Nijmegen, The Netherlands; least-square refinements : Sheldrick, G.M. SHELXL93, Program for the Refinement of Crystal Structures, 1993, University of Göttingen, Germany; calculation of geometric data : Spek, A.L. Platon, Program for the Automated Analysis of Molecular Geometry, 1996, University of Utrecht, The Netherlands; preparation of illustrations : Meetsma, A. PLUTO, Program for Display and Analysis of Crystal and Molecular Structures, 1996, University of Groningen, The Netherlands.