An efficient synthesis of substituted 3(4)-nitropyrroles from nitroalkenes and tosylmethyl isocyanides

Synthesis

Volumn , Issue 7, 1996, Pages 871-876

  Ten Have, Ronald ^a   Leusink, Frederik R ^a   Van Leusen, Albert M ^a  

^a UNIVERSITY OF GRONINGEN   (Netherlands)

Author keywords

[No Author keywords available]

Indexed keywords

PYRROLE DERIVATIVE;

ARTICLE; CRYSTALLOGRAPHY; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 0029920228     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (20)

1. Chemistry of Sulfonylmethyl Isocyanides 42. For part 41, see: van Leusen, D.; van Leusen, A. M. J. Org. Chem. 1994, 59, 7534.
2. Baer, H. H.; Urbas, L. In The Chemistry of the Nitro and Nitroso Group; Feuer, H. Ed.; Part 2, Interscience: New York, 1970; p 201. Boyer, J. H. Nitroazoles, VCH: New York; 1986.
3. Baer, H. H.; Urbas, L. In The Chemistry of the Nitro and Nitroso Group; Feuer, H. Ed.; Part 2, Interscience: New York, 1970; p 201. Boyer, J. H. Nitroazoles, VCH: New York; 1986.
4. Massa, S.; DiSanto, R.; Costi, R.; Mai, A.; Artico, M. Med. Chem. Res. 1993, 3, 192.
5. Almerico, A. M.; Cirrincione, G.; Aiello, E. J. Heterocycl. Chem. 1989, 26, 1631.
6. Ono, N.; Muratani, E.; Ogawa, T. J. Heterocycl. Chem. 1991, 28, 2053.
7. Leusink, F. R.; ten Have, R.; van den Berg, K. J.; van Leusen, A. M. J. Chem. Soc., Chem. Commun. 1992, 1401. Meetsma, A.; ten Have, R.; Leusink, F. R.; van Leusen, A. M. Acta Cryst. 1993, C49, 826.
8. Leusink, F. R.; ten Have, R.; van den Berg, K. J.; van Leusen, A. M. J. Chem. Soc., Chem. Commun. 1992, 1401. Meetsma, A.; ten Have, R.; Leusink, F. R.; van Leusen, A. M. Acta Cryst. 1993, C49, 826.
9. Moskal, J.; van Leusen, A. M. J. Org. Chem. 1986, 51, 4131.
10. Barton, D. H. R.; Kervagoret, J.; Zard, S. Z. Tetrahedron 1990, 46, 7587.
11. van Leusen, D.; Flentge, E.; van Leusen, A. M. Tetrahedron 1991, 47, 4639.
12. van Leusen, D.; van Echten, E.; van Leusen, A. M. J. Org. Chem. 1992, 57, 2245.
13. The beneficial influence of the use of 2 equivalents (or more) of base in the synthesis of pyrroles from TosMIC and Michael acceptors other than nitroalkenes was reported earlier: F. R. Leusink, Ph. D. Thesis, Groningen University, 1993, p 35.
14. van Leusen, A. M.; Wildeman, J.; Oldenziel, O. H. J. Org. Chem. 1977, 42, 1153.
15. van Leusen, D.; Schaart, F. J.; van Leusen, A. M. Recl. Trav. Chim. Pays-Bas 1979, 98, 258.
16. -1. The structure was determined by direct methods (Computer Software: SDP). Full-matrix least squares refined to R = 0.070, wR = 0.083 for 2125 observed reflections (I > 3σ(I)) collected using a Nonius CAD4F computer controlled kappa axis diffractometer, operating in the 2θ range 1.0 to 30.0° at 293 K.
17. Worrall, D. E. Org. Synth. Coll. Vol. I, 1947, p 413.
18. The 1-phenylprop-1-enyl group was tentatively assigned the E-configuration.
19. 5 This statement, by the way, implies that the nitro group in 2 exerts the strongest influence on the incoming Vilsmeier reagent.
20. Kochetkov, N. K.; Dubykina, N. V. J. Gen. Chem. USSR, 1958, 28, 2437.