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The Behaviour of E,Z-5-Arylmethylidene-2-thioxo-1,3-thiazolidin-4-one and 3-[(2-Oxo-2H-1-benzopyran-3-yl)dithio]-2H-1-benzopyran-2-one Derivatives towards Some Amines
Kandeel, K. A. The Behaviour of E,Z-5-Arylmethylidene-2-thioxo-1,3-thiazolidin-4-one and 3-[(2-Oxo-2H-1-benzopyran-3-yl)dithio]-2H-1-benzopyran-2-one Derivatives towards Some Amines Chemical Papers, Vol.58, No. 5, 2004, 334-340
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Document type:
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Článok z časopisu / Journal Article |
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Collection:
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Chemical papers
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| Attached Files |
| Name |
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MIMEType |
Size |
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n585a334.pdf
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585a334.pdf |
application/pdf |
182.16KB |
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| Author(s) |
Kandeel, K. A.
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| Title |
The Behaviour of E,Z-5-Arylmethylidene-2-thioxo-1,3-thiazolidin-4-one and 3-[(2-Oxo-2H-1-benzopyran-3-yl)dithio]-2H-1-benzopyran-2-one Derivatives towards Some Amines
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| Journal name |
Chemical Papers
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| Publication date |
2004
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| Year available |
2004
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| Volume number |
58
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| Issue number |
5
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| ISSN |
0366-6352
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| Start page |
334
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| End page |
340
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| Place of publication |
Poland
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| Publisher |
Versita
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| Collection year |
2004
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| Language |
english
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| Subject |
250000 Chemical Sciences
250300 Organic Chemistry
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| Abstract/Summary |
The reaction of 2-thioxo-1,3-thiazolidin-4-one with salicylaldehyde or its 5-bromo derivative in acetic acid and sodium acetate gave a mixture of E,Z- or E-5-arylmethylidene-2-thioxo-1,3- thiazolidin-4-ones (IIIa or IIIb) and the disulfide derivatives IVa and IVb, respectively. Treatment of IIIa with benzylamine or morpholine in dioxane at room temperature afforded 3-benzylamino- 2H-1-benzopyran-2-one (VIa) or E,Z-2-thiazolin-4-one derivative together with the amine salt, respectively. Similar treatment of IIIb with benzylamine yielded the E,Z-2-thiazolin-4-one derivative and the disulfide IVb as the major product. The disulfide IVa reacted with benzylamine in cold dioxane to yield the disulfide derivative of 4-benzylamino-2H-benzopyran-2-one in addition to VIa, whereas in boiling dioxane it gave VIa and the corresponding bisbenzyl derivative. On the other hand, when IIIb or IVa was treated with dicyclohexylamine in dioxane, it gave IVb as well as the amine salt in the former case and 3-sulfanyl-2H-1-benzopyran-2-one in the latter one. Structures of all products were evidenced by elemental analysis and spectral data.
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