A facile method for synthesis of heterocycles containing tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidine and coumarin moieties

Heterocyclic Communications

Volumn 5, Issue 3, 1999, Pages 241-242

  Vasylyev, Maxym V ^a   Bilokin, Yaroslav V ^a,b   Branytska, Olena V ^a   Kovalenko, Sergiy M ^a   Chernykh, Valentyn P ^a  

^a NATIONAL UNIVERSITY OF PHARMACY   (Ukraine)

^b WEIZMANN INSTITUTE OF SCIENCE   (Israel)

Author keywords

Benzothienopyrimidines; Benzothiophenes; Coumarins; Imines; Rearrangements

Indexed keywords

EID: 0033412565     PISSN: 07930283     EISSN: None     Source Type: Journal    
DOI: 10.1515/HC.1999.5.3.241     Document Type: Article

References (16)

1. A review on recent advances in tyrosine kinase inhibitors by D. W. Fry, Ann. Rep. Med. Chem. 31, 151 (1996)
2. (a) For synthesis of 3H-benzo[4,5]thieno[3,2-d]pyrimidin-4-ones, see: A. J. Bridges, H. Zhou, J. Heterocycl. Chem. 34, 1163 (1997);
3. and (b) For a review on synthesis and pharmacological aspects of heterocycles possessing thieno-fragment, see, also: R. Pech, R. Böhm, Pharmazie 39, 4 (1984)
4. Y. V. Bilokin, S. N. Kovalenko, I. E. Bylov, V. P. Chernykh, Heterocycl. Commun. 4, 257 (1998) and references cited therein
5. For synthesis of 2-imino-2H-1-benzopyran-3-carboxamides 1, see: 1a: (a) G. P. Schiemenz, Chem. Ber. 95, 483 (1962); and (b) P. Czerney, H. Hartmann, J. Prakt. Chem. 323, 691 (1981). 1b: C. N. O'Callaghan, Proc. Roy. Irish. Acad. 77B, 533 (1977)
6. For synthesis of 2-imino-2H-1-benzopyran-3-carboxamides 1, see: 1a: (a) G. P. Schiemenz, Chem. Ber. 95, 483 (1962); and (b) P. Czerney, H. Hartmann, J. Prakt. Chem. 323, 691 (1981). 1b: C. N. O'Callaghan, Proc. Roy. Irish. Acad. 77B, 533 (1977)
7. For synthesis of 2-imino-2H-1-benzopyran-3-carboxamides 1, see: 1a: (a) G. P. Schiemenz, Chem. Ber. 95, 483 (1962); and (b) P. Czerney, H. Hartmann, J. Prakt. Chem. 323, 691 (1981). 1b: C. N. O'Callaghan, Proc. Roy. Irish. Acad. 77B, 533 (1977)
8. For a procedure to synthesize 2-amino-4,5,6,7-tetrahydrobenzo[b]thiophene-3-carboxamide 2 from cyclohexanone, 2-cyanoacetamide, and sulfur by the application of Gewald reaction, see: V. P. Arya, Indian J. Chem. 10, 1141 (1972)
9. 1H NMR-and IR-analyses and by elemental microanalysis. Mp (°C) of compounds synthesized: 3a: > 300; 3b: 273-4; 4a: 267-8; 4b: 242-3
10. 2)
11. A manuscript on a facile method for synthesis of tetrahydrobenzo[b]thiophenes of type 3 is in preparation and will appear in due course: M. V. Vasylyev, Y. V. Bilokin, S. M. Kovalenko, O. V. Branytska, V. P. Chernykh, 'manuscript in preparation'
12. A. A. Karasev, L. L. Lukatskaya, M. I. Rubtsov, E. K. Zhikol, S. N. Yarmolenko, O. A. Ponomarev, Zh. Obshch. Khim. 65, 1547 (1995); Chem. Abstr. 124, 342517p (1996)
13. A. A. Karasev, L. L. Lukatskaya, M. I. Rubtsov, E. K. Zhikol, S. N. Yarmolenko, O. A. Ponomarev, Zh. Obshch. Khim. 65, 1547 (1995); Chem. Abstr. 124, 342517p (1996)
14. E. S. Hand, W. P. Jencks, J. Am. Chem. Soc. 84, 3505 (1962)
15. 2)
16. The structure of compound 4b was additionally corroborated by X-ray diffraction analysis and the data will be published elsewhere