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Intramolecular Reaction of tert‐Butyl‐NNO‐Azoxy and Cyano Groups – Novel Synthesis of Pyridazine, 1,2,3‐Triazepine, and Furan Rings Full article

Journal European Journal of Organic Chemistry
ISSN: 1434-193X , E-ISSN: 1099-0690
Output data Year: 2018, Volume: 2018, Number: 43, Pages: 5947-5953 Pages count : 7 DOI: 10.1002/ejoc.201800947
Authors Anikin Oleg V. 1 , Klenov Michael S. 1 , Churakov Aleksandr M. 1 , Guskov Alexey A. 1 , Strelenko Yurii A. 1 , Lyssenko Konstantin A. 2 , Tartakovsky Vladimir A. 1
Affiliations
1 N. D. Zelinsky Institute of Organic Chemistry Russian Academy of Sciences 47 Leninsky prosp. 119991 Moscow Russian Federation
2 A. N. Nesmeyanov Institute of Organoelement Compounds Russian Academy of Sciences 28 Vavilova St. 119991 Moscow Russian Federation

Abstract: A reaction of (tert-butyl-NNO-azoxy)acetonitrile with N,N-dimethylacetamide dimethylacetal afforded 2,4-bis(tert-butyl-NNO-azoxy)-3-methylpent-2-enedinitrile 9 as a main product. This compound cyclized on silica gel surface with the loss of isobutylene to give 6-amino-5-(tert-butyl-NNO-azoxy)-4-methylpyridazine-3-carbonitrile 2-oxide 10. On the contrary, the cyclization of dinitrile 9 in protic solvents resulted in quite different products: furan, 1,2,3-triazepine, and pyridazine derivatives were among them. These reactions are the first examples of intramolecular reactions of (tert-butyl-NNO-azoxy) and cyano groups. The structures of products under investigation were confirmed by X-ray diffraction analysis.
Cite: Anikin O.V. , Klenov M.S. , Churakov A.M. , Guskov A.A. , Strelenko Y.A. , Lyssenko K.A. , Tartakovsky V.A.
Intramolecular Reaction of tert‐Butyl‐NNO‐Azoxy and Cyano Groups – Novel Synthesis of Pyridazine, 1,2,3‐Triazepine, and Furan Rings
European Journal of Organic Chemistry. 2018. V.2018. N43. P.5947-5953. DOI: 10.1002/ejoc.201800947 WOS Scopus OpenAlex
Identifiers:
≡ Web of science: WOS:000451059700008
≡ Scopus: 2-s2.0-85055875452
≡ OpenAlex: W2891622086
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