Amine-Mediated Sequential One-Pot Synthesis of Highly Substituted Thiophenes from β-Keto Esters, Aryl Isothiocyanates and 4-Chloroacetoacetate

GRAPHICAL ABSTRACT

Abstract

The synthesis of a variety of highly substituted thiophenes has been achieved successfully via amine-mediated sequential one-pot reaction of β-keto esters, aryl isothiocyanates, and 4-chloroacetoacetate. Ease of handling, regioselectivity, metal-catalyst free, and good yields are the advantageous of this protocol. The structures were corroborated spectroscopically (IR, ¹H- and ¹³C-NMR, and EI-MS) and by elemental analysis. In this one-pot reaction, one new C–S and two C–C bonds are formed.

Keywords:

• Propylamine
• β-keto esters
• aryl isothiocyanates
• methyl 4-chloroacetoacetate
• thiophene
• one-pot synthesis