A facile synthesis of isoxazolo [5′,4′:4,5]thiazolo[3,2-a]thieno pyrimidines a new ring system

Article abstract of DOI:10.1080/10426509808033738

In a one-pot synthesis 6,7-dimethyl-2-arylidine-5-H-thieno[2,3-d]pyrimidine-3,5-diones 2 were prepared via the reaction of a ternary mixture of 5,6-dimethyl-2-thioxo-1,2,3,4-tetrahydrothienol[2,3-d]pyrimidin-4-one (1), chloroacetic acid, and a proper aldehyde. Compound 2 reacted with hydroxylamine to afford 2,3-dihydro-7,8-dimethyl-3-substituted-9H-isoxazolo[5′,4′:4,5] thiazolo [3.2-a] thieno[2,3-d]pyrimidin-9-ones (4). Reaction of 1 with 3-chloropent-2,4-dione in ethanolic potassium hydroxide yielded the S-acetylacetone derivative 5d. The latter compound reacted with hydrazines and thiourea affording the 2-pyrazolthio and the 2-pyrimidinylthio derivatives 11 and 12, respectively. Compound 5d also underwent cyclization on boiling with acetic anhydride/pyridine solution to yield 2-acetyl-3,6,7-trimelhyl-5H-thieno[2,3-d]thiazolo[3,2-a]pyrimidin-5-one (13). The 2-methylthioderivative 5a was converted into the corresponding 2-methyl sulphone derivative 9 on treatment with hydrogen peroxide.

Full text of DOI:10.1080/10426509808033738

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Phosphorus, Sulfur, and Silicon
and the Related Elements
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A FACILE SYNTHESIS
OF ISOXAZOLO
[5′,4′:4,5]THIAZOLO[3,2-
a]THIENO PYRIMIDINES A NEW
RING SYSTEM
A. M. Abdel-fattah a , As. Aly b , F. A. Gad b , M. E.
A. Zaki b & A. B. A. El-gazzar b
a Department of chemistry, Cairo University, Cairo,
Egypt
b Photochemistry Department, National Research
Center, Cairo, Egypt
Published online: 24 Sep 2006.
To cite this article: A. M. Abdel-fattah , As. Aly , F. A. Gad , M. E. A. Zaki & A. B.
A. El-gazzar (1998): A FACILE SYNTHESIS OF ISOXAZOLO [5′,4′:4,5]THIAZOLO[3,2-
a]THIENO PYRIMIDINES A NEW RING SYSTEM, Phosphorus, Sulfur, and Silicon and the
Related Elements, 141:1, 263-281
To link to this article: http://dx.doi.org/10.1080/10426509808033738
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