Multistep synthesis of thiazoloquinazolines under microwave irradiation in solution

Tetrahedron Letters

Volumn 41, Issue 7, 2000, Pages 1027-1030

  Besson, Thierry ^a   Guillard, Jérôme ^a   Rees, Charles W ^b  

^a UPRES 2001   (France)

^b IMPERIAL COLLEGE LONDON   (United Kingdom)

Author keywords

Medium ring heterocycles; Microwave heating; Quinazolines; Thiazoles

Indexed keywords

QUINAZOLINE DERIVATIVE;

ANALYTIC METHOD; ARTICLE; BROMINATION; DERIVATIZATION; DRUG SYNTHESIS; HEATING; MICROWAVE IRRADIATION; REACTION ANALYSIS; REACTION TIME;

EID: 0034639633     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)02221-2     Document Type: Article

References (18)

1. Appel, R.; Janssen, H.; Siray, M.; Knoch, F. Chem. Ber. 1985, 118, 1632-1643. The salt 1 is a pale greenish yellow solid, insoluble in organic solvents. It is completely stable in a dry inert atmosphere but reacts slowly with moisture to form 4-chloro-1,2,3-dithiazol-5-one.
2. (a) Rees, C. W. J. Heterocycl. Chem. 1992, 29, 639-651;
3. (b) Besson, T.; Emayan, K.; Rees, C. W. J. Chem. Soc., Perkin Trans. 1 1995, 2097-2102;
4. (c) Besson, T.; Rees, C. W. J. Chem. Soc., Perkin Trans. 1 1996, 2857-2860;
5. (d) Rakitin, O. A.; Rees, C. W.; Vlasova, O. G. Tetrahedron Lett. 1996, 37, 4589-4592;
6. (e) English, R. F.; Rakitin, O. A.; Rees, C. W.; Vlasova, O. G. J. Chem. Soc., Perkin Trans. 1 1997, 201-205;
7. (f) Besson, T.; Guillaumet, G.; Lamazzi, C.; Rees, C. W. Synlett 1997, 704-706.
8. Besson, T.; Guillard, J. Tetrahedron 1999, 55, 5139-5144.
9. (a) Besson, T.; Dozias, M.-J.; Guillard, J.; Jacquault, P.; Legoy, M. D.; Rees, C. W. Tetrahedron 1998, 54, 6475-6484.
10. (b) Bénéteau, V.; Besson, T.; Rees, C. W. Synth. Commun. 1997, 27, 2275-2280.
11. Spectral data for compounds 5-9 are consistent with the assigned structures.
12. +, 100%), 176 (23), 148 (27), 121 (18).
13. Besson, T.; Dozias, M.-J.; Guillard, J.; Rees, C. W. J. Chem. Soc., Perkin Trans. 1 1998, 3925-3926.
14. For the only other report of this ring system, see: Kanazawa, H.; Senga, K.; Tamura, Z. Chem. Pharm. Bull. 1985, 33, 618-625.
15. A full paper describing the complete synthesis and the biological evaluation of several thiazoloquinazoline derivatives will be published later.
16. (a) Commarmot, R.; Didenot, R.; Gardais, J. F. French patent 2 560 529 (1985), Rhône-Poulenc/Prolabo, Chem. Abst. 1986, 105, 17442;
17. (b) Jacquault, P. (Prolabo company) European Patent. 545995 AI (21-12-92), 1992.
18. Focused microwave irradiations were carried out at atmospheric pressure with a Synthewave S402 (capacity of the quartz reactors used: 10 and 70 ml) Prolabo microwave reactor (300 W, monomode system) which has a quartz reactor, visual control, irradiation (300 W) monitored by PC computer, infrared measurement and continuous feedback temperature control (by PC). Equipment of the oven was completed by an external stirring system, a condenser and dropping funnel allowing conditions close to those involved in classical methods; it is also possible to work under dry atmosphere or in vacuo if necessary. The ratio between the quantity of reactant and the solvent is very important; if it is too large, hazardous solvent bumping in the reactor may result. The best conditions involve a concentration of 3-5% of the starting material.