Paper
Studies on Heterocyclic Enaminonitriles, XV. A Convenient One-pot Synthesis of Ethyl 4-Amino-2,3-dihydrothieno-[2,3-b]pyridine-5-carboxylates
Published Dec 13, 1993 · H. Maruoka, K. Yamagata, M. Yamazaki
European Journal of Organic Chemistry
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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.
This study presents a convenient one-pot synthesis of ethyl 4-amino-2,3-dihydrothieno-[2,3-b]pyridine-5-carboxylates using titanium(IV) chloride and 2-amino-4,5-dihydro-3-thi
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