チオフェン誘導体の合成化学的研究(第6報) : 2,3-Bis(2-thienyl)acrylic Acid, 2-(2-Thienyl)-3-(5-nitro-2-thienyl)acrylic Acidおよびそれら誘導体の合成について

抄録

The Perkin reaction of 2-thiophenecarboxaldehyde and 2-thiopheneacetic acid afforded two kinds of stereoisomers of 2, 3-bis (2-thienyl) acrylic acid (IV) ; α-form (IVa) and β-form (IVb). Amidation of these compounds produced cis-2, 3-bis (2-thienyl) acrylamide (IVa) and trans-2, 3-bis (2-thienyl) acrylamide (VIb) from IVa and only IVb from IVb. The same reaction of 5-nitro-2-thiophenecarboxaldehyde (X) and 2-thiopheneacetic acid also afforded two isomers of 2-(2-thienyl)-3-(5-nitro-2-thienyl) acrylic acid (III) ; α-form (IIIa) and β-form (IIIb). Amidation of these compounds also afforded the cis-(XIa) and trans-2-(2-thienyl)-3-(5-nitro-2-thienyl) acrylamide (XIb) from IIIa and only XIb from IIIb. That these compounds were mutual stereoisomers was proved by the measurement of ultraviolet (UV) and infrared (IR) absorption spectra, and dipole moments.