Advances in Heterocyclic Chemistry: 95
Total synthesis of the four stereoisomers of centrolobine by Schmidt et al. Synthesis of a C-aryl glycoside by Schmidt et al. Arylation of chromene 73 by Correia et al.
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Arylation of the 4H-chromene 73 was realized in EtOH with 2,6-di- tert-butylmethylpyridine as proton sponge. In this case, EtOH 2. Second arylation of 2,3-dihydropyrroles by Correia et al. Synthesis of Kavalactones 77 and 79 by Correia et al. Selected examples of styrylcoumarins by Xu et al. Correia Boc-protecting group followed by an intramolecular cyclization gave et al. Toward this end, functionality provided the corresponding aryl pyrrolizidines 95a,b. Pd OAc 2 1. CF3CO 2O arylated pyrroles 88 in good overall yields.
General strategy for the arylation of 2,5-dihydropyrroles by Correia et al. The best conditions reported by the Scheme Synthesis of aryl pyrrolizidines by Correia et al. Pd OAc 2 corresponding lactam. Synthesis of aryl kainoids by Correia et al.
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Synthesis of Rolipram 98 by Correia et al. Acidic hydrolysis of the triester was 44 accompanied by a spontaneous decarboxylation to afford the trans- aryl kainoid acid AcO OAc 1. Correia et al. Synthesis of dihydroxylated prolines by Correia et al. The arylated pyrrolidine can be oxida- mesylationereduction steps furnished the compound Then, oxidative cleavage of the aryl ring unmasks the isomer followed by an acidic hydrolysis allowed the installation of corresponding carboxylic acid that can be further reduced into the targeted trans-diol function Last, the methylcarbamate was primary alcohol.
Unfortunately, the N N reaction yields are highly structure-dependant and the scope of this OMe Me OMe methodology appears to be quite narrow. Synthesis of indoles by Correia et al. Cleavage of the lated oxindoles Scheme ZnBr2, CH2Cl2 1. Overall HRC strategy by Felpin et al. In order to attain high conversion, high loading of from Pd OAc 2 and charcoal, gave excellent results Scheme It is one of the rare exam- depressant Scheme After phenylation of and basic hy- 1. Synthesis of oxindoles by Felpin et al. Arylation of tetrahy- dropyridines, derived from natural product arecoline , occurred smoothly to give the desired Heck adduct Scheme However, faster reaction rates were usually ionic liquids Scheme Protection of the nitrogen as a carbamate the counterion and found that lipophilic ionic liquids gave the best was mandatory for the success of the coupling since arecoline results.
However, in spite of excellent overall catalytic activity with as a free base was inert under Heck arylation. Arylation of arecoline derivatives by Correia et al. Interestingly, aryl 1. Synthesis of the aripiprazole key fragment by Schmidt et al. Synthesis of quinolone skeletons by Felpin et al.
Conclusion catalytic activity for reductive processes and SuzukieMiyaura cross- couplings where a Pd 0 pre-catalyst is usually preferred. However, it has been observed, in the last ten years, an one-pot sequential diazotation-Heck-reduction-cyclization re- increasing interest for the chemistry of diazonium salts especially actions Scheme Compared to using aryl diazonium salts could, indeed, be considered as an im- proved procedure over the traditional HeckeMizoroki coupling since transformations can be carried out at usually lower temper- 1. Although quite high palladium loadings have been frequently reported, recent improvements, especially from our BnO NO2 2.
Further progress would lead to a deeper understanding Cl N of the role of the counterion in the catalytic cycle involving cationic Cl N palladium species. Moreover, safety issues related to the use of O N O H diazonium salts need to be considered, especially for large scale Aripiprazole applications. All in all, we believe that the HeckeMatsuda reaction Scheme Synthesis of the aripiprazole key fragment by Felpin et al. Pschorr, R. Gomberg, M. Huisgen, R. Kikukawa, K. Acknowledgements Rondestveldt, C. The Abou Tetrahedron , 37, 31e We thank Dr.
Robin Li and Melissa Ma Science Library
Universite Int. Felpin, F. Pla-Quintana, A.
Yasui, S. Tetrahedron Lett. Barbero, M. Synthesis ,e Artuso, E. Tetrahedron , 62, e References and notes Sengupta, S. Tetrahedron , 53, e Synthesis , e; b Sengupta, S. For selected reviews, see: a Farina, V. Miyabe, T. Synlett , e; e Konno, T. Fluorine Chem. Zeni, G. Indian J. Mizoroki, T. Heck, R. Tetrahedron , 57, e; c b Sengupta, S. Synthesis , e Bartoli, G. Synlett , e Heck, Ei- Andrus, M. Kabalka, G.
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