Synthesis and intramolecular cyclization of novel β,β-bis-(benzo[b]thienyl)dehydroalanine derivatives

✍ Scribed by Ana S. Abreu; Natália O. Silva; Paula M.T. Ferreira; Maria-João R.P. Queiroz

• Book ID: 104253382
• Publisher: Elsevier Science
• Year: 2003
• Tongue: French
• Weight: 132 KB
• Volume: 44
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(03)00564-1

✦ Synopsis

The methyl ester of tert-butyloxycarbonyl-b,b-dibromodehydroalanine was obtained in a one-pot procedure from bis-(N-tert-butyloxycarbonyl)dehydroalanine. The former was reacted with several boronic benzo[b]thiophene acids under Suzuki cross coupling conditions, to give new b,b-bis-(benzo[b]thienyl)dehydroalanines in high yields. These compounds were cyclized to pyrrole derivatives by treatment with Pd(OAc) 2 and Cu(OAc) 2 in DMF.