Preparation of 5‐sulfonylpyrimidines from β‐keto, β‐cyano‐, and β‐ethoxycarbonyl‐β‐sulfonylenamines
- 1 January 1986
- journal article
- research article
- Published by Wiley in Journal of Heterocyclic Chemistry
- Vol. 23 (1) , 77-80
- https://doi.org/10.1002/jhet.5570230116
Abstract
β‐Keto‐β‐sulfonylenamines 2a,b reacted with benzamidine or guanidines to give 2,4‐disubstituted 5‐methanesulfonylpyrimidines 3a‐d, whose methanesulfonyl groups were substituted by n‐butyllithium or alkylmagnesium bromides to yield 2,4‐disubstitued 5‐alkylpyrimidines 6a‐d. 2‐Substituted 4‐amino‐5‐sulfonylpyrimidines 7a,b, 8 and 2‐substituted 5‐benzenesulfonylpyrimidin‐4‐ones 9a,b were similarly obtained from β‐cyano‐β‐sulfonylenamines 2c,d and β‐ethoxycarbonyl‐β‐sulfonylenamine (2e), respectively.Keywords
This publication has 20 references indexed in Scilit:
- SYNTHESIS OF N-ARYL ENAMINOSULFONES AND IMPROVED PREPARATION OF N-SUBSTITUTED ENAMINONITRILESOrganic Preparations and Procedures International, 1984
- A Convenient Synthesis of β-Sulfonylenamines from α,β-EpoxysulfonesSynthesis, 1983
- Nucleophilic behaviour of enamines derived from 2-methyl-5,6-dihydro-2H-thiopyran-3(4H)-one 1,1-dioxideJournal of the Chemical Society, Perkin Transactions 1, 1983
- Reaction of 1-Lithio-1-arylthio(or alkylthio)methyltrimethylsilane with Acid Derivatives. A Novel Synthesis of Functionalized Vinyl SulfidesBulletin of the Chemical Society of Japan, 1982
- Studies on pyrimidine derivatives. XXIV. Synthesis of 3-substituted 1,2,4-triazines by nucleophilic substitution.CHEMICAL & PHARMACEUTICAL BULLETIN, 1982
- Structure and reactivity of enamines derived from 5,6-dihydro-2H-thiapyran-3(4H)-one 1,1-dioxideJournal of the Chemical Society, Perkin Transactions 1, 1982
- Studies on pyrimidine derivatives. X. Coupling reaction of 5-halopyrimidines with olefinic compounds in the presence of palladium acetate and triphenylphosphine.CHEMICAL & PHARMACEUTICAL BULLETIN, 1979
- Synthese und Reaktivität von Phenylsulfonyl‐cyan‐keten‐S,S‐acetalenZeitschrift für Chemie, 1977
- Nucleophilic substitutions in the 2-methanesulfonylpyrimidine seriesCollection of Czechoslovak Chemical Communications, 1972
- α‐Substituted methylsulphonylacetonitriles: (Properties of the sulphonyl group XLII)Recueil des Travaux Chimiques des Pays-Bas, 1954