Synthesis of isomeric enamine derivatives of fused cycloalkeno thieno[2,3-d]pyrimidin-4(3H)-ones. Stereoelectronic effect on the regioselectivity

Synthesis

Volumn , Issue 17, 2007, Pages 2699-2705

  Lilienkampf, Annamaria ^a   Heikkinen, Sami ^a   Mutikainen, Ilpo ^a   Wähälä, Kristiina ^a  

^a UNIVERSITY OF HELSINKI   (Finland)

Author keywords

Electrophilic additions; Imines; Ketones; Regioselectivity; Tautomerism

Indexed keywords

ELECTROPHILIC ADDITIONS; REGIOSELECTIVE SYNTHESIS; TAUTOMERISM;

DERIVATIVES; ISOMERIZATION; REGIOSELECTIVITY; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL); X RAY CRYSTALLOGRAPHY;

AMINES;

1,2,3,4,7,8,9,10 OCTAHYDRO 12H [1]BENZOTHIENO[2,3 D]PYRIDO[1,2 A]PYRIMIDIN 12 ONE; 1,2,3,4,7,8,9,10,11,12 DECAHYDRO 14H [1]BENZOTHIENO[2',3':4,5]PYRIMIDO[1,2 A]AZOCIN 14 ONE; 2,3,4,7,8,910,11 OCTAHYDRO[1]BENZOTHIENO[2',3':4,5]PYRIMIDO[1,2 A]AZEPIN 13(1H) ONE; 2,3,6,7,8,9 HEXAHYDRO[1]BENZOTHIENO[2,3 D]PYRROLO[1,2 A]PYRIMIDIN 10(1H) ONE; 2,3,8,9 TETRAHYDRO[1]BENZOTHIENO[2,3 D]PYRROLO[1,2 A]PYRIMIDINE 6,10(1H,7H0 DIONE; 2,3,8,9,10,11 HEXAHYDRO[1]BENZOTHIENO[2',3':4,5]PYRIMIDO[1,2 A]AZEPINE 4,13(1H,7H) DIONE; 2,3,9,10,12 HEXAHYDRO 8H [1]BENZOTHIENO[2',3':4,5]PYRIMIDO[1,2 A]AZOCINE 4,14(1H,7H) DIONE; 3 [(DIMETHYLAMINO)METHYLENE] 2,3,8,9 TETRAHYDRO[1]BENZO THIENO[2,3 D]PYRROLOL[1,2 A]PYRIMIDINE 6,10(1H,7H) DIONE; 3 [(DIMETHYLAMINO)METHYLENE] 2,9,10,11,12 PENTAHYDRO 8H [1]BENZOTHIENOL[2',3':4,5]PYRIMIDO[1,2 A]AZOCINE 4,14(1H,7H) DIONE; 3 [9DIMETHYLAMINO)METHYLENE] 2,8,9,10,11 PENTAHYDRO[1]BENZOTHIENO[2',3':4,5]PYRIMIDO[1,2 A]AZEPINE 4,13(1H,7H) DIONE; 4,5,10,11 TETRAHYDRO 2H [1]BENZOTHIENO[2,3 D]PYRIDO[1,2 A]PYRIMIDIN 8,12(3H,9H) DIONE; 5 [(DIMETHYLAMINO)METHYLENE] 4,10,11 TRIHYDRO 2H [1]BENZOTHIENOL[2,3 D]PYRIDO[1,2 A]PYRIMIDIN 8,12(3H,9H) DIONE; 5,6,7,8 TETRAHYDRO 2,3, DIMETHYL[1]BENZOTHIENO[2,3 D]PYRIMIDIN 4(3H) ONE; 6,7 DIHYDRO 2,3 DIMETHYL[1]BENZOTHIENO[2,3 D]PYRIMIDINE 4,8(3H,5H) DIONE; 6,7 DIHYDRO 3 [2 (DIMETHYLAMINO)ETHENYL] 2 METHYL[1]BENZOTHIENO{2,3 D]PYRIMIDINE 4,8(3H,5H) DIONE; ACETAL DERIVATIVE; ENAMINE; KETONE DERIVATIVE; N,N DIMETHYLFORMAMIDE DIMETHYLACETAL; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; CRYSTAL STRUCTURE; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; POLYMERIZATION; SYNTHESIS; X RAY CRYSTALLOGRAPHY;

EID: 34548699343     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-983823     Document Type: Article

References (43)

1. Wähälä, K.; Lilienkampf, A.; Alho, S.; Huhtinen, K.; Johansson, N.; Koskimies, P.; Vihko, K. US Patent Appl. A120050032778, 2005.
2. Pindur, U. N,N-Dimethylformamide Diethyl Acetal, In Handbook of Reagents for Organic Synthesis, Reagents, Auxiliaries and Catalysts for C-C Bond Formation; Coates, R. M.; Denmark, S. E., Eds.; Wiley: Chichester, 1999, 315-318.
3. (a) Martin, J. C.; Barton, K. R.; Gott, P. G.; Meen, R. H. J. Org. Chem. 1966, 31, 943.
4. (b) Moltenini, V.; Hamilton, M. M.; Mao, L.; Crane, C. M.; Termin, A. P.; Wilson, D. M. Synthesis 2002, 12, 1663.
5. (c) Peterlin-Masic, L.; Mlinsek, G.; Solmajer, T.; Trampus-Bakija, A.; Stegnar, M.; Kikelj, D. Bioorg. Med. Chem. Lett. 2003, 13, 789.
6. (a) Olivera, R.; SanMartin, R.; Dominguez, E. J. Org. Chem. 2000, 65, 7010.
7. (b) Spivey, A. C.; Diaper, C. M.; Adams, H. J. Org. Chem. 2000, 65, 5253.
8. (c) Schenone, P.; Mosti, L.; Menozzi, G. J. Heterocycl. Chem. 1982, 19, 1355.
9. (d) Menozzi, G.; Mosti, L.; Schenone, P. J. Heterocycl. Chem. 1987, 24, 1669.
10. (e) Gopalsamy, A.; Yang, H.; Ellingboe, J. W.; Tsou, H.-R.; Zhang, N.; Honeres, E.; Powell, D.; Miranda, M.; McGinnis, J. P.; Rabindran, S. K. Bioorg, Med. Chem. Lett. 2005, 15, 1591.
11. (a) Lin, Y.-I.; Lang, S. A. Jr. J. Heterocycl. Chem. 1977, 14, 345.
12. (b) Dominguez, E.; Ibeas, E.; Martinez de Marigorta, E.; Kepa Palacios, J.; SanMartin, R. J. Org. Chem. 1996, 61, 5435.
13. (a) Spivey, A. C.; Srikaran, R.; Diaper, C. M.; Turner, D. J. Org. Biomol. Chem. 2003, 1, 1638.
14. (b) Porcheddu, A.; Giacomelli, G.; De Luca, L.; Ruda, A. M. J. Comb. Chem. 2004, 6, 105.
15. (c) Gudmundsson, K. S.; Johns, B. A. Org. Lett. 2003, 5, 1369.
16. (d) Johns, B. A.; Gudmundsson, K. S.; Turner, E. M.; Allen, S. H.; Samano, V. A.; Ray, J. A.; Freeman, G. A.; Boyd, F. L. Jr.; Sexton, C. J.; Selleseth, D. W.; Creech, K. L.; Moniri, K. R. Bioorg. Med. Chem. 2005, 13, 2397.
17. (a) Fossa, P.; Menozzi, G.; Dorigo, P.; Floreani, M.; Mosti, L. Bioorg. Med. Chem. 2003, 11, 4749.
18. (b) Bondavalli, F.; Bruno, O.; Lo Presti, E.; Menozzi, G.; Mosti, L. Synthesis 1999, 1169.
19. (c) Sircar, I.; Duell, B. L.; Bristol, J. A.; Weishaar, R. E.; Evans, D. B. J. Med. Chem. 1987, 30, 1023.
20. (a) Aoyama, H.; Nishio, T.; Hirabayashi, Y.; Hasegawa, T.; Noda, H.; Sugiyama, N. J. Chem. Soc., Perkin Trans. 1 1975, 298.
21. (b) Cohnen, E.; Dewald, R. Synthesis 1987, 566.
22. (c) Elghamry, I. Synth. Commun. 2002, 32, 897.
23. (d) Gabbutt, C. D.; Hepworth, J. D.; Heron, B. M.; Pugh, S. L. J. Chem. Soc., Perkin Trans. 1 2002, 2799.
24. (e) Gupton, J. T.; Krumpe, K. E.; Burnham, B. S.; Dwornik, K. A. Tetrahedron 1998, 54, 5075.
25. Schuda, P. A.; Ebner, C. B.; Morgan, T. M. Tetrahedron Lett. 1986, 27, 2567.
26. (a) Gompper, R.; Heinemann, U. Angew. Chem., Int. Ed. Engl. 1981, 20, 296.
27. (b) Molina, P.; Fresdena, P. M. J. Heterocycl. Chem. 1984, 21, 461.
28. Albright, J. D.; Sheperd, R. G. J. Heterocycl. Chem. 1973, 10, 899.
29. Kantlehner, W.; Haug, E.; Speh, S.; Bräuner, H. J. Liebigs Ann. Chem. 1985, 65.
30. Chenard, B. L.; Welch, W. M.; Blake, J. F.; Butler, T. W.; Reinhold, A.; Ewing, F. E.; Menniti, F. S.; Pagnozzi, M. J. J. Med. Chem. 2001, 44, 1710.
31. Vetelino, M. G.; Coe, J. W. Tetrahedron Lett. 1994, 35, 219.
32. (a) Hermecz, I.; Bitter, I.; Horvath, A.; Toth, G.; Meszaros, Z. Tetrahedron Lett. 1979, 27, 2557.
33. (b) Hermecz, I.; Vasvasri-Debreczy, L.; Simon, K.; Pongor-Csakvari, M.; Meszaros, Z. J. Chem. Soc., Perkin Trans. 1 1983, 369.
34. (c) Hermecz, I.; Horvath, A.; Meszaros, Z.; De Vos, C.; Rodriguez, L. J. Med. Chem. 1984, 27, 1253.
35. (a) Yamazaki, T.; Takahata, H.; Ishikura, M.; Nagata, M. Heterocycles 1978, 9, 1717.
36. (b) Takahata, H.; Ishikura, M.; Yamazaki, T. Chem. Pharm. Bull. 1980, 28, 220.
37. (c) Takahata, H.; Ishikura, M.; Nagai, K.; Nagata, M.; Yamazaki, T. Chem. Pharm. Bull. 1981, 29, 366.
38. Jeener, J.; Meier, B. H.; Bachmann, P.; Ernst, R. R. J. Chem. Phys. 1979, 71, 4546.
39. Günther, H. NMR Spectroscopy: Basic Principles, Concepts, and Applications in Chemistry, 2nd ed.; Wiley: Chichester, 1995, 333-334.
40. Crystallographic data has been deposited with the Cambridge Crystallographic Data Centre as supplementary publication numbers CCDC 643240 (3b), CCDC 643241 (3c), CCDC 643242 (3d), and CCDC 643243 (3e). These data can be obtained free of charge from The Cambridge Crystallographic Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
41. (a) Csukonyi, K.; Lazar, J.; Bernath, G.; Hermecz, I.; Meszaros, Z. Monatsh. Chem. 1986, 117, 1295.
42. (b) Manhas, M. S.; Amin, S. G. J. Heterocycl. Chem. 1992, 13, 903.
43. Kapustina, M. V.; Kharizomenova, I. A.; Shvedoov, V. I.; Radkevich, T. P.; Shipilova, L. D. Pharm. Chem. J. 1992, 26, 73.