Synthesis of Erlenmeyer-Plöchl Azlactones Promoted by 5-Sulfosalicylic Acid

Kiyani, Hamzeh; Aslanpour, Shiva

doi:10.3987/com-17-13711

Cited by 9 publications

(1 citation statement)

References 59 publications

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“…Recently, flow technology protocols for the preparation of Erlenmeyer oxazolones, as well as novel organocatalytic methodologies have been reported. For example, sulfanilic acid and 5‐sulfosalicylic acid were employed as heterogeneous catalysts, allowing the heterocycle preparation at room temperature and with the use of water as solvent. It is also worth to mention that these catalysts could be filtered‐off and reused.…”

Section: Introductionmentioning

confidence: 99%

Recent Advances in Azlactone Transformations

2019

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Azlactones, also known as oxazolones, are versatile building blocks in organic synthesis due to the presence of multiple pro‐nucleophilic and electrophilic reactive sites. Recently, several elegant organo‐ and metal‐catalyzed studies have been described, allowing the stereocontrolled access to complex structures in only one or a few chemical steps. Moreover, the development of one‐pot, tandem and domino reactions greatly enhanced the azlactone scaffold potential. In this context, this review aims to cover novel methodologies, including a brief overview of oxazolones and Erlenmeyer azlactones preparation. New approaches towards classical reactions, such as dynamic kinetic resolution, cycloadditions, and conjugate additions will be presented as well as new methodologies involving photochemical and flow chemistry technology. Finally, for most studies, selected examples will be presented and mechanistic pathways and/or activating modes will be carefully discussed.

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Section: Introductionmentioning

confidence: 99%