A new anionic cyclization reaction: Condensation of benzoate esters with nitriles to give 3-amino-2-inden-1-ones

✍ Scribed by Nadim E. Kayaleh; Ramesh C. Gupta; John F. Morrissey; Francis Johnson

• Publisher: Elsevier Science
• Year: 1997
• Tongue: French
• Weight: 190 KB
• Volume: 38
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(97)10181-2

✦ Synopsis

A/~trac~ A new type of anionic ¢yelization has been discovered in which the condensation of alkyl benzoates with simple nitriles, induced by an excess of LDA, leads directly to substituted-3-amino-2-indan-l-ones. The corresponding intermediL.t,~-[~-oxmitriles undergo cyclization to give, in most instances, superior yields of the same compounds. Acid hydrolysis of these indenones leads in high yield to the corresponding biologically active (anticoagulant) indandiones.