[4 + 2]-cycloaddition reactions involving α-oxo thioketone intermediates

Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences

Volumn 57, Issue 8, 2002, Pages 922-927

  Hegab, Mohamed I ^a   Amr, Abd El Galil A ^a   Abdel Megeid, Farouk M E ^a  

^a NATIONAL RESEARCH CENTRE   (Egypt)

Author keywords

1,3,4 Oxadithiins; Delta sign3 Thiopyran Derivatives; Oxo Thioketone Intermediates

Indexed keywords

CHLORINE COMPOUNDS; CYCLOADDITION;

1,3,4-OXADITHIINS; CHALCONE DERIVATIVES; DIETHYL ACETYLENEDICARBOXYLATE; IODIDE ION; THIOKETONE; TWO-PRODUCT; [4 + 2] CYCLOADDITION;

REACTION INTERMEDIATES;

2',2' DIMETHYLSPIRO[CHROMAN 3',3 (7 OXA 2 THIABICYCLO[2.2.1]HEPT 5 ENE] 4' ONE; 3,4 DIMETHYLDISPIRO[CYCLOHEPTANE 1'',2' CHROMAN 3,6 DELTA3 THIOPYRANE] 4' ONE; CARBOXYLIC ACID DERIVATIVE; CHALCONE DERIVATIVE; CHLORINE DERIVATIVE; DIMER; DISPIRO[CYCLOHEXANE 1'',2' CHROMAN 3',3 (7 OXA 2 THIABICYCLO[2.2.1]HEPT 5 ENE)] 4' ONE; IODIDE ION; KETONE DERIVATIVE; THIOKETONE; TRISPIRO[CYCLOHEPTANE 1,5' 2H CHROMENO[3,4 E][1,3,4]OXADITHIIN 2',3'' CHROMAN 2'',1''' CYCLOHEPTANE] 4'' ONE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CYCLIZATION; CYCLOADDITION; DIMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; PROTON TRANSPORT;

EID: 0036700863     PISSN: 09320776     EISSN: None     Source Type: Journal    
DOI: 10.1515/znb-2002-0813     Document Type: Article

References (20)

1. D. C. Dittmer, G. E. Kuhlmann, G. C. Levy, J. Org. Chem. 35, 3676 (1970).
2. a) N. Jacobsen, P. deMayo, A. C. Weedon, Nouv. J. Chim. 2, 331 (1978); Chem. Abstr. 90, 38851z (1979); b) A. A. El-Kateb, I.T. Henawy, R. Shabana, F. H. Osman, Phosphorus Sulfur 20, 329 (1984).
3. a) N. Jacobsen, P. deMayo, A. C. Weedon, Nouv. J. Chim. 2, 331 (1978); Chem. Abstr. 90, 38851z (1979); b) A. A. El-Kateb, I.T. Henawy, R. Shabana, F. H. Osman, Phosphorus Sulfur 20, 329 (1984).
4. a) N. Jacobsen, P. deMayo, A. C. Weedon, Nouv. J. Chim. 2, 331 (1978); Chem. Abstr. 90, 38851z (1979); b) A. A. El-Kateb, I.T. Henawy, R. Shabana, F. H. Osman, Phosphorus Sulfur 20, 329 (1984).
5. M. I. Hegab, F. M. E. Abdel-Megeid, F. A. Gad, S. A. Shiba, J. Møller, A. Senning, Sulf. Lett. 22, 9 (1998).
6. F. A. G. El-Essawy, S. M. Yassin, I. A. El-Sakka, A. F. Khattab, I. Støfte, J. Moller, A. Senning, Sulf. Lett. 22, 19 (1998)
7. F. A. G. El-Essawy, S. M. Yassin, I. A. El-Sakka, A. F. Khattab, I. Støfte, J. Møller, A. Senning, J. Org. Chem. 63, 9840 (1998).
8. B. Saville, M. Steer, J. Chem. Soc., Chem. Commun. 616 (1972).
9. C. Bak, K. Praefcke, Chem. Ber. 112, 2744 (1979).
10. B. Hahn, B. Köpke, J. Voß, Justus Liebig's Ann. Chem. 10 (1981).
11. C. Bak, K. Praefcke, J. Heterocycl. Chem. 17, 1655 (1980).
12. K. Thimm, J. Voß, Tetrahedron Lett., 537 (1975).
13. K. Thimm, W. Schmüser, J. Voß, J. Chem. Res. [S], 244 (1977); [M] 2837
14. K. Thimm, W. Schmüser, J. Voß, J. Chem. Res. [S], 244 (1977); [M] 2837
15. U. Zehavi, J. Org. Chem. 42, 2821 (1977).
16. a) H. Aoyama, S. Suzuki, T. Hasegawa, Y. Omota, J. Chem. Soc., Chem. Commun. 899 (1979); b) H. Aoyama, S. Suzuki, T. Hasegawa, Y. Omota, J. Chem. Soc. Perkin Trans. 1, 247 (1982).
17. a) H. Aoyama, S. Suzuki, T. Hasegawa, Y. Omota, J. Chem. Soc., Chem. Commun. 899 (1979); b) H. Aoyama, S. Suzuki, T. Hasegawa, Y. Omota, J. Chem. Soc. Perkin Trans. 1, 247 (1982).
18. C. D. Gabbutt, J. D. Hepworth, B. M. Heron, M. Kanjia, Tetrahedron 50, 5245 (1994).
19. H. J. Kabbe, Synthesis 886 (1978).
20. J. B. Peter, D. H. John, J. Chem. Soc. Perkin Trans. 1, 827 (1983).