Concise synthesis of cycloheptatrienes from aldehydes and the Wittig reagent prepared from pyruvic ester

[Display omitted] •The synthesis of 1,3,5-cycloheptatriene (CHT) derivatives.•The condensation of 4-pentenal with the Wittig reagent derived from pyruvic ester.•Various CHTs are obtained by simple manipulations under the optimal conditions which are milder than previously reported. A novel and conci...

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Bibliographic Details
Published in:Tetrahedron letters 2021-06, Vol.73, p.153150, Article 153150
Main Authors: Yoshimura, Tomoyuki, Chino, Kanta, Matsuo, Jun-ichi
Format: Article
Language:English
Subjects:
1,3,5-Cycloheptatrienes
4-Pentenals
Pyruvic ester
Wittig reagent
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Summary:[Display omitted] •The synthesis of 1,3,5-cycloheptatriene (CHT) derivatives.•The condensation of 4-pentenal with the Wittig reagent derived from pyruvic ester.•Various CHTs are obtained by simple manipulations under the optimal conditions which are milder than previously reported. A novel and concise synthesis of 1,3,5-cycloheptatrienes has been developed. The reaction of 4-substituted-4-pentenal derivatives with the Wittig reagent prepared from pyruvic ester under the optimal conditions proceeded to give 1,6-di- and 1,6,7-trisubstituted-1,3,5-cycloheptatrienes in moderate yield. The synthesis is advantageous through its use of readily available reagents, milder reaction conditions compared to those previously reported, and simple manipulations. Additionally, a plausible mechanism via intramolecular [4+2]cycloaddition followed by the ring-expansion of norcarene is proposed based on the products of the reaction.
ISSN:0040-4039
1873-3581
DOI:10.1016/j.tetlet.2021.153150