Studies on condensation of chlorocarbonyl phenyl ketene with N-unsubstituted amides: synthesis of some new 1,3-oxazin-6-ones

Oxazine-6-one and 4-pyrimidinol are two important frameworks in pharmaceutical production. Herein, we disclosed a simple, efficient, inexpensive organic base-promoted and additivestimulated protocol for the syntheses of variably functionalized oxazine-6-ones and 4-pyrimidinols employing acetonitrile solvent under conventional heating conditions using an oil bath through C−N and C−O coupled domino steps. This simple practicable productive protocol utilizes easily producible cheap precursors, namely, benzimidates or benzamidines, with differently substituted dicyano-olefins, and it comprises step economy, robustness, and moisture insensitive conditions affording high yield that avoids the use of transition-metal catalysts, multistep with multicomponent strategy, and harsh reaction conditions involving hazardous chemicals. This method is scalable into gram-scale production with good yield.

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Studies on condensation of chlorocarbonyl phenyl ketene with N-unsubstituted amides: synthesis of some new 1,3-oxazin-6-ones

Abstract: A series of 1,3 oxazin 6 one derivatives has been synthesized upon treatment of N unsub stituted amides with chlorocarbonyl phenyl ketene under reflux in toluene for several minutes. In this simple way, 2,5 disubstituted derivatives of 1,3 oxazin 6 ones have been obtained in high yields.

Cited by 3 publications

References 13 publications

ChemInform Abstract: Studies on Condensation of Chlorocarbonyl Phenyl Ketene with N‐Unsubstituted Amides: Synthesis of Some New 1,3‐Oxazin‐6‐ones.

ChemInform Abstract: Studies on Condensation of Chlorocarbonyl Phenyl Ketene with N‐Unsubstituted Amides: Synthesis of Some New 1,3‐Oxazin‐6‐ones.

Ketenes as Privileged Synthons in the Synthesis of Heterocyclic Compounds Part 3

Organic Base-Promoted C–N- and C–O-Coupled Domino Cyclization Strategy: Syntheses of Oxazine-6-ones and 4-Pyrimidinols

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