New Synthetic Technology for the Rapid Construction of Novel Heterocycles—Part 2. The Reaction of IBX with Anilides and Related Compounds

✍ Scribed by K. C. Nicolaou; Yong-Li Zhong; Phil S. Baran

• Publisher: John Wiley and Sons
• Year: 2000
• Tongue: English
• Weight: 111 KB
• Volume: 112
• Category: Article
• ISSN: 0044-8249
• DOI: 10.1002/(sici)1521-3757(20000204)112:3<639::aid-ange639>3.0.co;2-3

✦ Synopsis

Experimental Section

DMP (2.0 equiv) was added in one portion to a solution of 7 a (0.1 mmol) in benzene (4 mL) or BTF. [6] The solution was heated at reflux (or at 80 ± 85 8C for the reactions in BTF) for about 30 min at which point TLC indicated complete consumption of starting material. Dilution with EtOAc followed by washing with 5 % aq. NaHCO 3 (2 Â ) and brine, drying over MgSO 4 , and concentration led to crude 7 b. Pure 7 b was isolated in 40 % yield after column chromatography (silica gel, EtOAc:hexane 1:2) (see Table 3 for selected physical properties).