A facile synthesis of spiroisoxazolines: Intramolecular cyclization of 3-aryl-2-nitroacrylates promoted by titanium tetrachloride

✍ Scribed by Seiko Hirotani; Eisuke Kaji

• Publisher: Elsevier Science
• Year: 1999
• Tongue: French
• Weight: 917 KB
• Volume: 55
• Category: Article
• ISSN: 0040-4020
• DOI: 10.1016/s0040-4020(99)00119-2

✦ Synopsis

Titanium tetrachloride-induced cyclization of 3-(0-or m-substituted p-methoxyphenyl)-2nitro acrylates (1) provided stereoselectively (4¢t,5~)-l-oxa-2-azaspiro[4, 5]deca-2,6,9-trien-8-ones (2). Ortho-substituted p-methoxyphenyl nitroacrylates gave 2 in good yield. 3-(4'-methoxy-l'-naphthyl)-2nitroacrylate also reacted with titanium tetrachloride to give quantitatively (4ct,513)-4'-oxospiro[isoxazole-(4H)5,1'(4'H)-naphthalene]. 3-(10'-methoxy-9'-anthryl )-2-nitroacrylate was converted to 10-oxospiro-[anthracene-(10H)9,5'(4'/-/)-isoxazole].