Regioselectivity of the Diels-Alder reactions of 2,5,8(1H)-quinolinetriones

✍ Scribed by José María Pérez; Luis Vidal; Mercedes T. Grande; J.Carlos Menéndez; Carmen Avendaño

• Publisher: Elsevier Science
• Year: 1994
• Tongue: French
• Weight: 743 KB
• Volume: 50
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(01)85276-5

✦ Synopsis

IYiels-Alder reactions of 2,5,8(1If)quinoliaet were completely rcgiosekcuve for au the unsymmetrical &llert&e&uceptinthecaseofisopfaKlIliscmtspondstoa levelofregtosdectivity hi*tban theefoundhybyviauwo&xforSSquindinecplinm. A number of studies are available on the regioselectivity of the Diels-Alder reactions of 1,4naphthoquinones,t and 1,4_anthraquinones,~ many of them prompted by synthetic work in the field of the anthracyclines and related antibiotics.3 In contrast_ the regiocltemistry of the Diels-Alder cycloadditions between heterocyclic quittones and unsymmetrical aliphatic dienes has received very little attention. In the case of quinolinequinones, Potts and coworkers4 have shown that the electron distribution in 5,Squinolinequinone provides complete control of the cycloaddition of electron-rich dienes, such as I-methoxy-1.3-cyclohexadiene and l-methoxy-3-trimethylsilyloxy-1,3butadiene