Investigation of reactions of CH-acids with generated in situ N-[1,2-bis(methoxycarbonyl)vinyl]pyridinium in the synthesis of 1,2,3,4,5,6,7-hepta(methoxycarbonyl)cycloheptatriene

Investigation of reactions of CH-acids with generated in situ N-[1,2-bis(methoxycarbonyl)vinyl]pyridinium in the synthesis of 1,2,3,4,5,6,7-hepta(methoxycarbonyl)cycloheptatriene Full article

Journal

Russian Chemical Bulletin
ISSN: 1573-9171 , E-ISSN: 1066-5285

Output data

Year: 2024, Volume: 73, Number: 5, Pages: 1455-1459 Pages count : 5 DOI: 10.1007/s11172-024-4265-z

Authors

Belyy A.Yu. ¹ , Sokolova A.D. ¹ , Salikov R.F. ¹ , Platonov D.N. ¹ , Tomilov Yu.V. ¹

Affiliations

1	N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

The study investigated the reactivity of various CH-acids/conjugated bases in the synthesis of hepta(methoxycarbonyl)cycloheptatriene through a cascade reaction. NMR spectral monitoring identified (methoxycarbonyl)methylpyridinium as the true nucleophilic component in the original synthesis based on methyl diazoacetate. The scope of CH-acids capable of participating in the reaction was expanded to include sulfonium salts and sulfones, whereas certain nucleophiles were found to be ineffective. A correlation between the pKa values of CH-acids and the formation of seven-membered rings in the cascade reaction was established.

Belyy A.Y. , Sokolova A.D. , Salikov R.F. , Platonov D.N. , Tomilov Y.V.
Investigation of reactions of CH-acids with generated in situ N-[1,2-bis(methoxycarbonyl)vinyl]pyridinium in the synthesis of 1,2,3,4,5,6,7-hepta(methoxycarbonyl)cycloheptatriene
Russian Chemical Bulletin. 2024. V.73. N5. P.1455-1459. DOI: 10.1007/s11172-024-4265-z WOS Scopus OpenAlex

≡ Web of science:	WOS:001252371600015
≡ Scopus:	2-s2.0-85192260828
≡ OpenAlex:	W4399899319