Regioselective preparation of 1-(bromomethyl)-5H-thiazolo[3,2- a]quinazolin-5-ones and analogous 5H-thieno[3,2-e]thiazolo[3,2-a]pyrimidin-5- ones from fused 2-(alkenylthio)pyrimidin-4-ones

Synthesis

Volumn , Issue 5, 2000, Pages 714-720

  Wippich, Petra ^a   Gütschow, Michael ^a   Leistner, Siegfried ^a  

^a UNIVERSITY OF LEIPZIG   (Germany)

Author keywords

2 (alkenylthio)pyrimidin 4 ones; Bromocyclization; Heterocycles; Polycyclic pyrimidinones; Thiazolo 3,2 a quinazolin 5 ones; Thieno 3,2 e thiazolo 3,2 a pyrimidin 5 ones

Indexed keywords

BROMINE; PYRIMIDINONE DERIVATIVE; QUINAZOLINONE DERIVATIVE;

ARTICLE; BROMINATION; COLUMN CHROMATOGRAPHY; CYCLIZATION; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS; SYNTHESIS; ULTRAVIOLET SPECTROSCOPY;

EID: 1642586726     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2000-6390     Document Type: Article

References (24)

1. For synthetic routes to tricyclic thiazolo(1,3-thiazino) pyrimidinones, see Ref. 3 and references therein. For a review on thiazolo(1,3-thiazino)quinazolines, see Ref. 4.
2. For thiazolo[3,2-a]pyrimidinones, see Ref. 5, for thiazolo[2,3-b]quinazolinones, see Ref. 3 and references therein.
3. Wippich, P.; Hendreich, C.; Gütschow, M.; Leistner, S. Synthesis 1996, 741.
4. Shaban, M. A. E.; Taha, M. A. M.; Sharshira, E. M. Adv. Heterocycl. Chem. 1991, 52, 5.
5. Danel, K.; Pedersen, E. B.; Nielsen, C. J. Med. Chem. 1998, 41, 191.
6. Leistner, S.; Gütschow, M.; Drößler, K.; Vieweg, H.; Wagner, G.; Strohscheidt, T.; Lohmann, D.; Laban, G.; Siegling, A.; European Patent 0454060, 1991; Chem. Abstr. 1992, 116, 83689.
7. Leistner, S.; Gütschow, M.; Drößler, K.; Vieweg, H.; Wagner, G.; Strohscheidt, T.; Lohmann, D.; Laban, G.; Siegling, A.; European Patent 0454060, 1991; Chem. Abstr. 1992, 116, 83689.
8. Gütschow, M.; Drößler, K.; Leistner, S. Arch. Pharm. (Weinheim) 1995, 328, 231.
9. Gütschow, M.; Leistner, S. Synthesis 1995, 1488.
10. 13C NMR data of alkenylthio derivatives 7 were similar to those of the linear compounds 2-5 (Table 2), indicating the tautomeric 3H-pyrimidin-4-one structure.
11. 13C NMR shifts have been considered to distinguish between angular and linear thiazolopyrimidinones, as well as thiazolo[1,2,4]benzothiadiazine 5,5-dioxides, see Refs 5, 11.
12. Chern, J.-W.; Tao, P.-L.; Wang, K.-C.; Gutcait, A.; Liu, S.-W.; Yen, M.-H.; Chien, S.-L.; Rong, J.-K. J. Med. Chem. 1998, 41, 3128.
13. 2 was assumed to occur via electrophilic attack of the intermediate carbocation at N-1 atom, see Ref 5. Following this mechanism, in the present transformations a direct attack of the stabilized secondary (formed from 7a-c, 10a) or tertiary carbocation (from 7d-f, 10b) at the N-1 or S, respectively, would provide the thiazolo products 8, 11. The formation of the six-membered 1,3-thiazine ring in 14 could be explained accordingly.
14. From the NMR data of 11c, the purified compound appears as one of two possible diastereomers. Its predominant formation might be explained by assuming a bromonium ion intermediate and and addition of the sulfur atom which gives the racemic (2R, 1'S), (2S, 1'R) pair.
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23. Crotyl chloride (Merck) containing 90% of the trans isomer was used.
24. Frank, R. L.; Smith, P. V. Org. Synth. 1948, 28, 89.