Application of primary allyl amines from Morita-Baylis-Hillman adducts: Cyanogen-azide-mediated synthesis of substituted 5-aminotetrazoles and their attempted transformation to tetrazolo[1,5-a]pyrimidinones
IR@CDRI: CSIR-Central Drug Research Institute, Lucknow
View Archive Info| Field | Value | |
| Creator |
Nag, Somnath
Bhowmik, Subhendu Gauniyal, H M Batra, Sanjay |
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| Date |
2014-07-21T04:24:19Z
2014-07-21T04:24:19Z 2010 |
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| Identifier |
European Journal of Organic Chemistry 2010, 2010, (24), 4705–4712
http://hdl.handle.net/123456789/1311 |
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| Description |
A general protocol for the synthesis of substituted 5-aminotetrazoles by reacting cyanogen azide with the primary allyl amines afforded either by SN2 or SN2′- reaction of Morita- Baylis-Hillman acetate of acrylate has been developed. The base-promoted intramolecular cyclization of these tetrazoles afford highly substituted 2-azido-pyrimidin-4(3H)-ones instead of the expected tetrazolo-pyrimidinone due to azide-tetrazole tautomerism. Nevertheless it has been discovered that substituted tetrazolo[1,5-a]pyrimidin-7(4H)-ones could be isolated in pure form from a methanolic solution of respective 2-azido-pyrimidin-4(3H)-ones via crystallization. The structure of tetrazolo[1,5-a]pyrimidin-7(4H)-one has been unambiguously assigned via X-ray crystallography analysis. The existence of azide-tetrazole tautomerism in this class of compounds has been supported through NMR studies.
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274217 bytes
application/pdf |
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| Language |
en
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| Relation |
CSIR-CDRI Communication No. 7942
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| Subject |
Morita-Baylis-Hillman
Allyl amine Cyanogen azide Tetrazole Tautomerism |
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| Title |
Application of primary allyl amines from Morita-Baylis-Hillman adducts: Cyanogen-azide-mediated synthesis of substituted 5-aminotetrazoles and their attempted transformation to tetrazolo[1,5-a]pyrimidinones
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Article
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