5985-25-1Relevant articles and documents
Self-Condensation of Enaminodiones as a Method for Benzene Ring Construction: Synthesis of Diacyl-Substituted Phenols and Catechols
Obydennov, Dmitrii L.,Chernyshova, Elena V.,Sosnovskikh, Vyacheslav Y.
, p. 6491 - 6501 (2019/05/24)
A novel transition metal-free approach for the construction of the benzene core has been developed through self-condensation of available enaminodiones. Functionalized acyl-substituted phenols and catechols were obtained in 29-97% yields with high chemoselectivity under mild conditions. This base-promoted formal [4+2] annulation proceeds via cyclohexanone formation and involves the cascade transformation based on double Michael addition and aromatization (retro-Claisen cleavage and amine elimination).
Aromatic nucleophilic substitution or CuI-catalyzed coupling route to martinellic acid
Ma, Dawei,Xia, Chengfeng,Jiang, Jiqing,Zhang, Jianhua,Tang, Wenjun
, p. 442 - 451 (2007/10/03)
Condensation of β-amino ester 8b with triflate 7 gives N-aryl amino ester 11, which is converted into 2-substituted 4-oxoquinoline 4 using an intramolecular Dieckmann reaction as the key step. CuI-mediated coupling of β-amino ester 8a with 1,4-diiodobenzene followed by an intramolecular acylation and Pd-catalyzed carbonylation provide another manner to 4. Alkylation of 4 and subsequent reductive amination deliver the cyclic imine 14, which is transformed into triamine 3 by ordinary operations. Guanylation of 3 under mild condition followed by deprotection results in the synthesis of martinellic acid 1.