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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
Author(s) -
Maruoka Hiroshi,
Yamagata Kenji,
Yamazaki Motoyoshi
Publication year - 1993
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.1993199301207
Subject(s) - chemistry , diethyl malonate , ethyl acetoacetate , pyridine , ethyl cyanoacetate , medicinal chemistry , malonate , benzoyl chloride , chloride , organic chemistry , catalysis , malononitrile
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 .