One-pot stereoselective synthesis and structural study of 1-methylthio-2-azabuta-1,3-diene-4-carbonitriles
- 1 January 1992
- journal article
- research article
- Published by Royal Society of Chemistry (RSC) in Journal of the Chemical Society, Perkin Transactions 1
- No. 24,p. 3377-3381
- https://doi.org/10.1039/p19920003377
Abstract
The methylation of the carbanion resulting from addition of thioamides to methoxymethylene compounds 1 or ketene dithioacetals 2 affords two series of 1-methylthio-2-azabuta-1,3-diene-4-carbonitriles 5 or 6. The IR, MS and 1H and 13C NMR spectral properties are reported. X-Ray crystallographic analyses established the E stereochemistry of the C–N double bond in all cases studied. Isomerization of the C–N double bond was achieved by treatment of the 2-aza dienes 5a and 6a with sodium methanethiolate in propan-2-ol at room temperature.Keywords
This publication has 25 references indexed in Scilit:
- Reaction of anions from monoimines of benzil with alkylating agents. Photochemical reactivity of some 4-alkoxy-2-aza-1,3-dienesJournal of the Chemical Society, Perkin Transactions 1, 1992
- 1,4-Dehydrochlorination of α-chloroimines as a suitable procedure for the synthesis of unactivated 2-aza-1,3-dienes and 3-aza-1,3,5-trienesTetrahedron Letters, 1990
- Synthesis and reactions of 3‐alkoxy‐2H‐azirinesRecueil des Travaux Chimiques des Pays-Bas, 1986
- Aroylation of carbanions derived from N-(diphenylmethyl)arylmethanimines. A synthesis of 4-aroyloxy-2-azabuta-1,3-dienesJournal of the Chemical Society, Perkin Transactions 1, 1986
- Preparation and reactivity of 2‐Aza‐1,3‐butadienes: A Diels‐Alder route to 5,6‐dihydro‐2 H ‐1,3‐oxazine derivativesEuropean Journal of Inorganic Chemistry, 1985
- [1 + 3] Cycloadditions of isocyanides to azomethine ylides; synthesis and properties of 1-phthalimidoazetidinesThe Journal of Organic Chemistry, 1983
- N,N-bis(silyl)enamines as protected primary vinylamines. Nucleophilic activation of the siliconnitrogen bond.Tetrahedron Letters, 1982
- A Diels-Alder route to pyridone and piperidone derivativesJournal of the American Chemical Society, 1982
- 1-Azetine: thermal ring opening to 2-azabutadieneJournal of the American Chemical Society, 1981
- Reactions retrodieniques—IXTetrahedron, 1980