Synthetic exploitation of the ring-opening of 3,4-dinitrothiophene. Access to 1,4-disubstituted 2,3-dinitro-1,3-butadienes and 2,3-diaminobutanes

Tetrahedron

Volumn 52, Issue 9, 1996, Pages 3313-3326

  Dell'Erba, Carlo ^a   Novi, Marino ^a   Petrillo, Giovanni ^a   Spinelli, Domenico ^b   Tavani, Cinzia ^a  

^a CNR   (Italy)

^b UNIVERSITY OF BOLOGNA   (Italy)

Author keywords

[No Author keywords available]

Indexed keywords

1,3 BUTADIENE DERIVATIVE; DIAMINE DERIVATIVE; NITRO DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0030019980     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(95)01113-7     Document Type: Article

References (50)

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34. The procedure employed is an appropriate modification of that reported for the reduction of monofunctional oxime ethers: Feuer, H.; Braunstein, D. M. J. Org. Chem. 1969, 34, 1817.
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36. a) Gladych, J. M. Z.; Hartley, D. Polyfunctional Amines. In Comprehensive Organic Chemistry, Sutherland, I. O. Ed.; Pergamon Press: Oxford, 1979, Vol. 2, p. 84. Porter, A. E. A. Pyrazines and their Benzo Derivatives. In Comprehensive Heterocyclic Chemistry, Boulton, A.J.; McKillop, A. Eds.; Pergamon Press: Oxford, 1984, Vol. 3, p. 179. Grimmett, M. R. Imidazoles and their Benzo Derivatives. In Comprehensive Heterocyclic Chemistry, Potts, K. T. Ed.; Pergamon Press: Oxford, 1984, Vol. 5, p. 469. Sharp, J. T. Seven-membered Rings with Two or More Heteroatoms. In Comprehensive Heterocyclic Chemistry, Lwowski, W. Ed.; Pergamon Press: Oxford, 1984, Vol. 7, p. 610.
37. a) Gladych, J. M. Z.; Hartley, D. Polyfunctional Amines. In Comprehensive Organic Chemistry, Sutherland, I. O. Ed.; Pergamon Press: Oxford, 1979, Vol. 2, p. 84. Porter, A. E. A. Pyrazines and their Benzo Derivatives. In Comprehensive Heterocyclic Chemistry, Boulton, A.J.; McKillop, A. Eds.; Pergamon Press: Oxford, 1984, Vol. 3, p. 179. Grimmett, M. R. Imidazoles and their Benzo Derivatives. In Comprehensive Heterocyclic Chemistry, Potts, K. T. Ed.; Pergamon Press: Oxford, 1984, Vol. 5, p. 469. Sharp, J. T. Seven-membered Rings with Two or More Heteroatoms. In Comprehensive Heterocyclic Chemistry, Lwowski, W. Ed.; Pergamon Press: Oxford, 1984, Vol. 7, p. 610.
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44. 6b for the analogous preparations of dinitrobutadienes 2, allowing the dichloromethane extracts to stand several hours at room temperature before workup generally ensures a complete stereomutation of some formed (E,Z)-and (Z,Z)-products into the more stable (E,E)-isomer. Actually, for 1,4-diaryl-substituted 2 such stereomutation goes to completion in 1-2 h. In the case of the 1,4-dialkyl analogues several hours are necessary; moreover when bulky substituents are present (as cyclohexyl in 2k abd sec-butyl in 2j) some (E,Z)-isomer remains in the final reaction mixture.
45. 6
46. 23 stereochemical assignments take also account of the high deshielding observed for the nitrovinylic protons in the (E,E) isomers and in the (E) portion of the (E,Z) isomers as compared to the same protons in the (Z) portion of the molecule.
47. Pretsch, E.; Clerc, T.; Seibl, J.; Simon, W. Spectral Data for Structure Determination of Organic Compounds, Springer-Verlag: Berlin, 1989, H20.
48. It should be stressed that under the used conditions the methylation reaction usually requires 30-45 min to go to completion; longer reaction times were used in order to ensure (as independently ascertained on some samples isolated at shorter times) a complete stereomutation of 14 into the most thermodinamically stable isomer.
49. 13C NMR of the crystallized material are in agreement with those reported: Roskamp, E. J.; Pedersen, S. F. J. Am. Chem. Soc. 1987, 109, 3152.
50. 3COOH is consistent with that reported: Jung, S.-H.; Kohn, H. J. Am. Chem. Soc. 1985, 107, 2931.