Synthesis of 3-Arylthieno[2,3-b]-, -[2,3-c]- or -[3,2-c]pyridines Utilizing an Interrupted Pummerer Reaction

Abstract

An efficient procedure for the synthesis of three types of thienopyridines has been developed. Thus, 3-(1-arylethenyl)-2-(ethylsulfinyl)pyridines, 4-(1-arylethenyl)-3-(ethylsulfinyl)pyridines, and 3-(1-arylethenyl)-4-(ethylsulfinyl)pyridines, which can be easily prepared from the respective aryl chloropyridinyl ketones in a three-step sequence, undergo an interrupted Pummerer reaction on treatment with excess acetic anhydride at temperatures ranging from 100 to 130 ˚C to give 3-arylthieno[2,3-b]pyridines, 3-aryl­thieno[2,3-c]pyridines, and 3-arylthieno[3,2-c]pyridines, respectively.

Key words

thieno[2,3-b]pyridines - thieno[2,3-c]pyridines - thieno[3,2-c]pyridines - interrupted Pummerer reaction - acetic anhydride

References

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