Synthesis and stereochemistry of 11,11a-dihydro derivatives of (4S)-2,4- dimethyl-2,4-dihydro-1H-pyrazino[2,1-b]quinazoline-3,6-diones. A new transannular rearrangement proposal

Journal of Organic Chemistry

Volumn 64, Issue 19, 1999, Pages 7233-7235

  Martín Santamaría, Sonsoles ^a   Espada, Modesta ^a   Avendaño, Carmen ^a  

^a UNIVERSIDAD COMPLUTENSE DE MADRID   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

11 (DIPHENYLMETHYL) 2,4 DIMETHYL 2,4,11,11A TETRAHYDRO 1H PYRAZINO[2,1 B]QUINAZOLINE 3,6 DIONE; 11 BENZYL 2,4 DIMETHYL 2,4,11,11A TETRAHYDRO 1H PYRAZINO[2,1 B]QUINAZOLINE 3,6 DIONE; 2,4 DIMETHYL 1 (3 CHLOROBENZYL) 2,4,11,11A TETRAHYDRO 1H PYRAZINO[2,1 B]QUINAZOLINE 3,6 DIONE; 2,4 DIMETHYL 1 (3 INDOLYLMETHYL) 2,4,11,11A TETRAHYDRO 1H PYRAZINO[2,1 B]QUINAZOLINE 3,6 DIONE; 2,4 DIMETHYL 2,4,11,11A TETRAHYDRO 1H PYRIZINO[2,1 B]QUINAZOLINE 3,6 DIONE; 2,4(1H,3H) QUINAZOLINEDIONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CONFORMATIONAL TRANSITION; DRUG CONFORMATION; DRUG SYNTHESIS; ISOMERISM; PKA; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION;

EID: 0344549349     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo981957b     Document Type: Article

References (19)

1. (a) Karwoski, J. P.; Jackson, M.; Rasmussen, R. R.; Humphrey, P. E.; Poddig, J. B.; Kohl, W. L.; Kadam, S.; McAlpine, J. B. J. Antibiot. 1993, 46, 374.
2. (b) You, M.; Wickramaratne, D. B. M.; Silva, G. L.; Chai, H.; Chagwedera, T. E.; Farnsworth, N. R.; Cordell, G. A.; Kinghorn, A. D.; Pezzuto, J. M. J. Nat. Prod. 1995, 58, 598.
3. Méndez-Vidal, C.; Rodríguez A. Cancer Lett. 1998, 132, 45.
4. (a) Martín-Santamaría, S.; Buenadicha, F. L.; Espada, M.; Söllhuber, M.; Avendaño, C. J. Org. Chem. 1997, 62, 6425.
5. (b) Martín-Santamaría, S.; Espada, M.; Avendaño, M. Tetrahedron 1997, 53, 16795.
6. (c) Bartolomé, M. T.; Buenadicha, F. L.; Avendaño, C.; Söllhuber, M. Tetrahedron: Asymmetry 1998, 9, 249.
7. (d) Buenadicha, F. L.; Avendaño, C.; Söllhuber, M.; Tetrahedron: Asymmetry 1998, 9, 4275.
8. (e) Fernández, M.; Heredia, M. L.; de la Cuesta, E.; Avendaño, C. Tetrahedron 1998, 54, 2777.
9. (e) Martín-Santamaría, S.; Espada, M.; Avendaño, C. Tetrahedron 1999, 55, 1755.
10. Buenadicha, F. L.; Bartomé, M. T.; Aguirre, M. J.; Avendaño, C.; Söllhuber, M. Tetrahedron: Asymmetry 1998, 9, 483.
11. Hutchins, R. O.; Hutchins, M. K. Comprehensive Organic Synthesis; Pergamon Press: Elmsford, NY, 1991; Vol. 8, pp 26 and references therein.
12. (a) Rajappa, S.; Advani, B. G. Tetrahedron 1973, 29, 1299.
13. (b) Rajappa, S.; Advani, B. G. J. Chem. Soc., Perkin Trans. 1 1974, 2122.
14. (c) Suguna, K.; Ramakumar, S.; Rajappa, S. Acta Crystallogr. B 1982, B38, 1654.
15. 2a
16. 1H NMR spectra being compared with those of compounds 2 and 4, respectively.
17. Anions A represent intermediates formula presented
18. Elvinga, P. J.; Pace, S. J.; O'Reilly, J. E. J. Am. Chem. Soc. 1973, 95, 647.
19. Edstrom, E. D. Tetrahedron Lett. 1991, 2, 5709.