A new synthesis of the benzofuran adenosine antagonist XH-14

Bioorganic and Medicinal Chemistry Letters

Volumn 7, Issue 24, 1997, Pages 3081-3084

  Hutchinson, Sally A ^a   Luetjens, Henning ^a   Scammells, Peter J ^a  

^a DEAKIN UNIVERSITY   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

2 (4 HYDROXY 3 METHOXYPHENYL) 5 (3 HYDROXYPROPYL) 7 METHOXY 3 BENZO[B]FURANCARBALDEHYDE; ADENOSINE RECEPTOR BLOCKING AGENT; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0031454605     PISSN: 0960894X     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0960-894X(97)10173-1     Document Type: Article

References (13)

1. Yang, Z.; Hon, P. M.; Chui, K. Y.; Xu, Z. L.; Chang, H. M.; Lee, C. M.; Cui, Y. X.; Wong, H. N. C.; Poon, C. D.; Fung, B. M. Tetrahedron Lett. 1991, 32, 2061.
2. Yang, Z.; Liu, H. B.; Lee, C. M.; Chang, H. M.; Wong, H. N. C. J. Org. Chem. 1992, 57, 7248.
3. Wong, H. N. C.; Niu, C. R.; Yang, Z.; Hon, P. M.; Chang, H. M.; Lee, C. M. Tetrahedron 1992, 48, 10339.
4. Jacobson, K.A.; van Galen, P.J.M.; Williams, M. J. Med. Chem. 1992, 35, 407.
5. Nagoa, Y.; Fujita, E.; Kohno, T.; Yagi, M. Chem. Pharm. Bull. 1981, 29, 3202.
6. +).
7. Decodts, G.; Wakselman, M. Bulletin De La Societe Chimique De France 1972, 12, 4586.
8. Nicholas, K. M. J. Am. Chem. Soc. 1975, 97, 3254.
9. Breitmaier, E.; Voelter, W. Carbon-13 NMR Spectroscopy (3rd Edition); VCH Verlagsgesellchaft mbH: Weinheim, 1989; pp 319-321.
10. Fujisaki, S.; Eguchi, H.; Omura, A.; Okamoto, A.; Dishida, A. Bull. Chem. Soc. Jpn. 1993, 66, 1576.
11. +).
12. Hutchinson, S. A.; Scammells, P. J.; Tiekink, E. Z. Krist. in press.
13. In our hands, the Gattermann-Adam reaction proved to be quite temperamental. The HCl gas required for this reaction was generated from concentrated sulphuric acid and solid ammonium chloride. Attempts using HCl from a commercial cyclinder (>99%) or generated from concentrated sulphuric acid and concentrated hydrochloric acid resulted in only deacetylation of 7.