Synthesis and transformations of 2-substituted tetrahydro-4H-benzo[4,5]thieno[2,3-d][1,3]oxazines and 2,3-disubstituted hexahydrobenzo [4,5]thieno[2,3-d]pyrimidines

Phosphorus, Sulfur and Silicon and the Related Elements

Volumn 178, Issue 2, 2003, Pages 245-259

  El Ahl, A A S ^a   Ismail, M A ^a,b   Amer, F A ^a  

^a Mansoura University   (Egypt)

^b GEORGIA STATE UNIVERSITY   (United States)

Author keywords

Octahydro 1H benzo 4 ,5 thieno 2 ,3 :4,5 pyrimido 1,2 b pyridazines; Synthesis; Thieno 2,3 d pyrimidines; Thieno 2,3 d 1,3 oxazines

Indexed keywords

2 [(4 ETHOXY 4 OXOBUTANOYL)AMINO] 4,5,6,7 TETRAHYDROBENZO[B]THIOPHENE 3 CARBOXYLIC ACID; 2 [3 (CARBOXYPROPANOYL)AMINO] 4,5,6,7 TETRAHYDROBENZO[B]THIOPHENE 3 CARBOXYLIC ACID; 2 HYDROXY 3 (4 OXO 5,6,7,8 TETRAHYDRO 4H BENZO[4,5]THIENO[2,3,B]PYRIDIN 4 YL)ACETATE; 2,3,4,7,8,9,10,11 OCTAHYDRO 1H BENZO[4',5']THIENO[2',3':4,5]PYRIMIDO[1,2, B]PYRIDAZIN 2,11 DIONE; 3 (3 AMINO 4 OXO 3,4,5,6,7,8 HEXAHYDRO 4H BENZO[4,5]THIENO[2,3 D]PYRIMIDIN 2 YL)PROPANOIC ACID; 3 (3 AMINO 4 OXO 3,4,5,6,7,8 HEXAHYDROBENZO[4,5]THIENO[2,3 D]PYRIMIDIN 2 YL)PROPANEHYDRAZIDE; 3 (3 AMINO 4 OXO 3,4,5,6,7,8 TETRAHYDRO 4H BENZO[4,5]THIENO[2,3 D]PYRIMIDIN 2 YL)PROPANOIC ACID; 3 [3 [(BETA DEXTRO ARABINOFURANOSYL)AMINO] 4 OXO 3,4,5,6,7,8 HEXAHYDROBENZO[4,5]THIENO[2,3 D]PYRIMIDIN 2 YL]PROPANOIC ACID; 3 [3 [(BETA DEXTRO GALACTOPYRANOSYL)AMINO] 4 OXO 3,4,5,6,7,8 HEXAHYDROBENZO[4,5]THIENO[2,3 D]PYRIMIDIN 2 YL]PROPANOIC ACID; 3 [3 [(BETA DEXTRO GLUCOPYRANOSYL)AMINO] 4 OXO 3,4,5,6,7,8 HEXAHYDROBENZO[4,5]THIENO[2,3 D]PYRIMIDIN 2 YL]PROPANOIC ACID; 3 [3 [1 (2 HYDROXYPHENYLMETHYLIDENE)AMINO] 4 OXO 3,4,5,6,7,8 HEXAHYDROBENZO[4,5]THIENO[2,3 D]PYRIMIDIN 2 YL]PROPANOIC ACID; 3 [3 [1 (4 BROMOPHENYLMETHYLIDENE)AMINO] 4 OXO 3,4,5,6,7,8 HEXAHYDROBENZO[4,5]THIENO[2,3 D]PYRIMIDIN 2 YL]PROPANOIC ACID; 3 [3 [1 (4 CHLOROPHENYLMETHYLIDENE)AMINO] 4 OXO 3,4,5,6,7,8 HEXAHYDROBENZO[4,5]THIENO[2,3,D]PYRIDIN 2 YL]PROPANOIC ACID; 3 [3 [1 (4 METHOXYPHENYLMETHYLIDENE)AMINO] 4 OXO 3,4,5,6,7,8 HEXAHYDROBENZO[4,5]THIENO[2,3 D]PYRIMIDIN 2 YL]PROPANOIC ACID; 3 [4 OXO 3 [(2 OXO 2,3 DIHYDRO 1H 3 INDOLYLIDENE)AMINO] 3,4,5,6,7,8 HEXAHYDROBENZO[4,5]THIENO[2,3 D]PYRIMIDIN 2 YL]PROPANOIC ACID; ETHYL 2 [[3 [[3 (ETHOXYCARBONYL) 4,5,6,7 TETRAHYDROBENZO[B]THIOPHEN 2 YL]AMINO] 3 OXOPROPANOYL]AMINO] 4,5,6,7 TETRAHYDROBENZO[B]THIOPHENE 3 CARBOXYLATE; ETHYL 3 (3 AMINO 4 OXO 3,4,5,6,7,8 HEXAHYDRO 4H BENZO[4,5]THIENO[2,3 D]PYRIMIDIN 2 YL)PROPANOATE; ETHYL 3 [3 (4 METHOXYPHENYL) 4 OXO 3,4,5,6,7,8 HEXAHYDROBENZO[4,5]THIENO[2,3 D]PYRIMIDIN 2 YL]PROPANOATE; ETHYL 3 [3 (4 METHYLPHENYL) 4 OXO 3,4,5,6,7,8 HEXAHYDROBENZO[4,5]THIENO[2,3 D]PYRIMIDIN 2 YL]PROPANOATE; OXAZINE DERIVATIVE; PROPIONIC ACID DERIVATIVE; PYRIMIDINE DERIVATIVE; THIOPHENE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYST; CYCLIZATION; HYDROLYSIS; INFRARED SPECTROSCOPY; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; THERMAL ANALYSIS;

EID: 0037300136     PISSN: 10426507     EISSN: None     Source Type: Journal    
DOI: 10.1080/10426500307943     Document Type: Article

References (15)

1. D. Haigh, D. G. Smith, and R. W. Ward, PCT Int. Appl. WO 98 54,192 (Cl. C07D 498/04) (December 1998); C. A. 130: 38389z (1999).
2. D. J. McNair, A. N. Shaw, A. D. Gribble, L. J. A. Jennings, M. J. Parratt, and R. L. Jarvest, PCT Int. Appl. WO 97 48,707 (Cl. C07D 498/04) (December 1997); C. A. 129: 16093a (1998).
3. R. L. Jarvest, L. J. A. Jennings, and I. L. Pinto, PCT Int. Appl. WO 97 27, 200 (Cl. C07D 498/04) (July 1997); C. A. 127: 190744g (1997).
4. R. L. Jarvest, I. L. Pinto, S. M. Ashman, C. E. Dabrowski, A. V. Fernndez, L. J. A. Jennings, P. Lavery, and D. G. Tew, Bioorg. Med. Chem. Lett., 9(3), 443 (1999).
5. M. Guetschow and U. Neumann, J. Med. Chem., 41(10), 1729 (1998).
6. M. R. Player and J. W. Sr. Sowell, J. Heterocycl. Chem., 32(5), 1537 (1995).
7. I. L. Pinto, R. L. Jarvest, B. Clarke, C. E. Dabrowski, A. Fenwick, M. M. Gorczyca, L. J. Jennings, P. Larvey, E. J. Sternberg, D. G. Tew, and A. West, Bioorg. Med. Chem. Lett., 9(3), 449 (1999).
8. B. L. Chenard and W. M. Welch, Jr., Eur. Pat. Appl. EP 900, 799 (Cl. C07D495/04) (March 1999); C. A. 130: 209718n (1999).
9. N. Suzuki and S. Furuya, PCT Int. Appl. WO 97 40,846 (Cl.A61K38/09) (November 1997). C. A. 128: 16433r (1998).
10. S. Furuya, N. Coho, K. Kato, and S. Hinuma, PCT Int. Appl. WO 96 24,597 (C. C07D495/04) (August 1996); C. A. 125: 247795q (1996).
11. A.-A. S. El-Ahl, Phosphorus, Sulfur and Silicon, 156, 189 (2000).
12. S. Hanessian and A. G. Parnet, Adv. Carbohydr. Chem. Biochem., 33, 111 (1976).
13. G. Ah-Kow, F. Terrier, M.-J. Pouet, and M.-P. Simonnin, J. Org. Chem., 45, 4399 (1980).
14. E. Breitmaier, Structure Elucidation By NMR in Organic Chemistry: A Practical Guide (New York: John Wiley and Sons, 1993), p. 46.
15. F.-L. Chung, R. A. Earl, and L. B. Townsend, J. Org. Chem., 45, 2532 (1980).