Sep-Oct 2006
An Efficient Synthesis of new Thiazolopyrimidinones under Microwave Irradiation
1229
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7-(2,2-Dimethyl[1,3]dioxan-5-ylidenemethyl)-6-nitro-5H-thia-
zolo[3,2-a]pyrimidin-5-one (26).
1
Yellow solid, mp 150 °C, H NMR (deuteriochloroform, 200
MHz) ꢀ 1.42 (s, 6H), 4.34 (s, 2H), 5.01 (s, 2H), 6.23 (s, 1H),
7.16 (d, J = 4.9 Hz, 1H), 8.06 (d, J = 4.9 Hz, 1H). 13C NMR
(deuteriochloroform, 50 MHz) ꢀ 21.6 (CH3), 22.9 (CH3), 63.3
(CH2), 65.2 (CH2), 99.0 (C), 117.6 (CH), 123.5 (CH), 125.6
(CH), 135.8 (C), 150.8 (C), 156.5 (C), 157.1 (C), 164.5 (C).
Anal. Calcd for C13H13N3O5S: C, 48.29; H, 4.05; N, 13.00.
Found: C, 48.05; H, 4.03; N, 12.93.
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Farmaco, 54, 588 (1999).
7-Benzenesulfonylmethyl-6-nitro-5H-thiazolo[3,2-a]pyrimidin-
5-one (27).
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Syrota and A. Feline, Biol. Psychiatry, 45, 180 (1999).
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191 (1998).
1
Yellow solid, mp 235 °C, H NMR (deuteriochloroform, 200
MHz) ꢀ 5.19 (s, 2H), 7.83 (d, J = 4.9 Hz, 1H), 8.094-8.07 (m,
5H), 8.48 (d, J = 4.9 Hz, 1H). 13C NMR (deuteriochloroform, 50
MHz) ꢀ 57.9 (CH2), 117.7 (CH), 123.5 (CH), 127.9 (2xCH),
129.1 (2xCH), 134.2 (CH), 138.6 (C), 150.9 (C), 155.2 (C),
157.0 (C), 164.5 (C).
Anal. Calcd for C13H9N3O5S2: C, 44.44; H, 2.58; N, 11.96.
Found: C, 44.42; H, 2.57; N, 11.95.
Ethyl-2-methyl-3-(6-nitro-5-oxo-5H-thiazolo[3,2-a]pyrimidin-7-
yl)acrylate (28).
1
Yellow solid, mp 157 °C, H NMR (deuteriochloroform, 200
MHz) ꢀ 1.33 (t, J = 7.1 Hz, 3H), 2.26 (s, 3H), 4.28 (q, J = 7.1
Hz, 2H), 7.17 (d, J = 4.9 Hz, 1H), 7.47 (s, 1H), 8.16 (d, J = 4.9
Hz, 1H). 13C NMR (deuterio-chloroform, 50 MHz) ꢀ 14.2 (CH3),
14.9 (CH3), 63.4 (CH2), 117.6 (CH), 123.5 (CH), 137.1 (CH),
141.1 (C), 150.7 (C), 155.0 (C), 157.1 (C), 164.4 (C), 169.1 (C).
Anal. Calcd for C12H11N3O5S: C, 46.60; H, 3.58; N, 13.59.
Found: C, 46.57; H, 3.56; N, 13.58.
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(1982).
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Farmaco, 48, 427 (1993).
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H. K. Pujari, Indian J. Exp. Biol., 10, 37 (1972).
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[27] P. Lidström, J. Tierney, B. Wathey and J. Westman,
Tetrahedron, 57, 9225 (2001).
[28] L. Perreux and A. Loupy, Tetrahedron, 57, 9199 (2001).
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58, 3177, (2002).
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Vanelle, Heterocycles, 55, 535 (2001).
Diethyl 2-[(6-nitro-5-oxo-5H-thiazolo[3,2-a]pyrimidin-7-yl)-
methylene]malonate (29)
1
Yellow solid, mp 168 °C, H NMR (deuteriochloroform, 200
MHz) ꢀ 1.23 (t, J = 7.1 Hz, 6H), 4.25 (q, J = 7.1 Hz, 4H), 7.15
(d, J = 4.9 Hz, 1H), 7.54 (s, 1H), 8.04 (d, J = 4.9 Hz, 1H). 13C
NMR (deuteriochloroform, 50 MHz) ꢀ 14.8 (CH3), 15.4 (CH3),
61.6 (CH2), 62.8 (CH2), 117.5 (CH), 123.5 (CH), 129.1 (CH),
144.0 (C), 150.9 (C), 155.2 (C), 157.1 (C), 162.4 (C), 164.5 (C),
165.1 (C).
Anal. Calcd for C14H13N3O7S: C, 45.78; H, 3.57; N, 11.44.
Found: C, 45.75; H, 3.55; N, 11.43.
[31] T. Terme, M. D. Crozet, A. Gellis and P. Vanelle, Recent.
Res. Devel. Organic Chem., 8, 437 (2004).
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