Abaee M Saeed, Nosood Yazdanbakhsh L, Akbarzadeh Elaheh, Mojtahedi Mohammad M, Al-Harrasi Ahmed
Organic Chemistry Department, Chemistry and Chemical Engineering Research Center of Iran P.O. Box 14335-186 Tehran Iran
Natural and Medical Sciences Research Center, University of Nizwa P.O. Box 33, Postal Code 616, Birkat Al Mauz Nizwa Sultanate of Oman.
RSC Adv. 2025 Sep 4;15(38):31806-31811. doi: 10.1039/d5ra04673d. eCollection 2025 Aug 29.
A new series of dihydronaphthalen-1(2)-one derivatives were synthesized in high yields starting from commercially available 3,5,5-trimethylcyclohex-2-en-1-one 1a, aromatic aldehydes 2, and diethyl acetylenedicarboxylate. Reaction of 1a with the aldehydes produced the respective dienones 3, which could cycloadd to dialkyl acetylenedicarboxylate, either stepwise or , under aqueous/organocatalyzed (DMAP) conditions. The respective adducts 4, were produced efficiently a Diels-Alder-double bond isomerization-oxidative aromatization sequence and were characterized based on the analysis of their H and C NMR spectra.
以市售的3,5,5-三甲基环己-2-烯-1-酮1a、芳香醛2和乙酰基二羧酸二乙酯为起始原料，高产率地合成了一系列新的二氢萘-1(2)-酮衍生物。1a与醛反应生成相应的二烯酮3，其可在水相/有机催化（4-二甲氨基吡啶）条件下，逐步或直接与乙酰基二羧酸二烷基酯发生环加成反应。通过狄尔斯-阿尔德-双键异构化-氧化芳构化序列高效生成相应的加合物4，并基于对其氢谱和碳谱的分析对其进行了表征。
