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Studies on Heterocyclic Enaminonitriles, XV. A Convenient One-pot Synthesis of Ethyl 4-Amino-2,3-dihydrothieno-[2,3-b]pyridine-5-carboxylates

✍ Scribed by Maruoka, Hiroshi ;Yamagata, Kenji ;Yamazaki, Motoyoshi

Publisher
John Wiley and Sons
Year
1993
Tongue
English
Weight
307 KB
Volume
1993
Category
Article
ISSN
0947-3440

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✦ Synopsis

Abstract

The reaction of 2‐amino‐4,5‐dihydro‐3‐thiophenecarbonitriles 1a–c with ethyl acetoacetate in the presence of titanium(IV) chloride gave the corresponding ethyl 4‐amino‐2,3‐dihydro‐6‐methylthieno[2,3‐b]pyridine‐5‐carboxylates 3a–c. Similarly, compounds 1a–c reacted with diethyl malonate or ethyl cyanoacetate to give the corresponding ethyl 4‐amino‐2,3,6,7‐tetrahydro‐6‐oxothieno[2,3‐b]pyridine‐5‐carboxylates 4a–c or ethyl 4,6‐diamino‐2,3‐dihydrothieno[2,3‐b]pyridine‐5‐carboxylates 5a–c.

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## Abstract magnified image 2‐Chloro‐4,6‐diarylnicotinonitrile 1 was reacted with ethyl 2‐mercaptoacetate 2 to furnish ethyl 2‐(3‐cyano‐4,6‐diarylpyridin‐2‐ylthio)acetate 3 as intermediates. These intermediates were cyclized by Thorpe–Zeigler cyclization using solid–liquid phase‐transfer catalysis