Synthesis of Cycloalkanone‐Substituted Ketene Aminals and their Reaction with Ethyl Propiolate
- 1 November 1987
- journal article
- organische chemie
- Published by Wiley in European Journal of Inorganic Chemistry
- Vol. 120 (11) , 1803-1807
- https://doi.org/10.1002/cber.19871201106
Abstract
2‐[Bis(methylthio)methylene]cycloalkanones 1 react with diamines to give the corresponding 2‐[tetrahydropyrimidin‐2(1H)‐ylidene]cycloalkanones 2a–e and 2‐(2‐imidazolidinylidene)cycloalkanones 2f, g. The ketene aminals 2 react with ethyl propiolate in alcoholic solution to afford 9‐[(alkoxycarbonyl)‐alkyl]pyrido[1,2‐a]pyridines 5a–e, 6c, e, and 8‐[(alkoxycarbonyl)alkyl]imidazo[1,2‐a]pyridines 5f, g 6g via ring cleavage of the cyclic ketones. This facile ring cleavage of cyclic ketones is unusual.Keywords
This publication has 12 references indexed in Scilit:
- Synthesis of 2-(Benzoylmethylene)imidazolidines and -hexahydropyrimidines by Condensation of Ethyl Benzoylacetimidates With 1,2-Ethanediamine or 1,3-Propandiamine, and Some Addition ReactionsSynthesis, 1987
- Synthesis of ketene aminals with an imidazolidine ring by condensation of 4,5‐dihydro‐2‐(methylithio)‐1H‐imidazoles with active methylene compounds and some addition and cyclocondensation reactionsEuropean Journal of Inorganic Chemistry, 1986
- Synthesis of Imidazo[1,2-a]pyridine and Pyrido[1,2-a]pyrimidine Derivatives by the Addition and Cyclocondensation Reactions of Ketenaminals Containing Imidazolidine or Hexahydropyrimidine Ring with Esters of a,b-Unsaturated AcidsHETEROCYCLES, 1986
- Heterocyclic β‐Enamino Esters, 34. New Types of Spiro Compounds by Addition and Cyclization Reactions of 3‐(2‐Imidazolidinylidene)‐ and 3‐(Tetrahydro‐2(1H)‐pyrimidinylidene)dihydro‐2(3H‐furanones with Methyl Acrylate and Dimethyl AcetylenedicarboxylateEuropean Journal of Inorganic Chemistry, 1984
- Heterocyclic β‐Enamino Esters, 33. Addition and Cyclization Reaction of 3‐(2‐Imidazolidinylidene)‐and 3‐(Hexahydro‐2‐pyrimidinylidene)‐2(3H)‐furanones with Hydrochloric Acid, Halogens, and Methyl PropiolateEuropean Journal of Inorganic Chemistry, 1984
- Heterocyclic β‐Enamino Esters, 321). Reactions of Aliphatic Diamines and Methylamine with 2‐Amino‐4,5‐dihydro‐3‐furancarboxylic Esters. Revised Constitutions by 13C NMR StudiesEuropean Journal of Inorganic Chemistry, 1984
- Synthesis of 1,1-diamino-2-thioacylethylenes: A novel C-thioacylation by the Willgerodt-Kindler reactionTetrahedron, 1982
- Synthese und Reaktionen von 2‐[Bis‐(alkylthio)‐methyliden]‐indan‐1,3‐dionenJournal für Praktische Chemie, 1979
- Synthese und Reaktionen carbocyclischer Acyl‐keten‐S,S‐acetaleJournal für Praktische Chemie, 1979
- Synthesen mit Enaminen, X. Systematische Synthese methylverzweigter CarbonsäurenEuropean Journal of Inorganic Chemistry, 1966