Substituted Ethyl 2-Acyl-3-amino-6-methylthieno(2,3-b)pyridine-4carboxylates as Synthons for Novel Heterocycles. -Title compounds of type (III) provide novel heterocyclic compounds (V) with diketene-acetone (IV). Except for (Vb), further reaction with (IV) is possible leading to novel tetracyclic co
Substituted ethyl 2-acyl-3-amino-6-methylthieno[2,3-b]pyridine-4-carboxylates as synthons for novel heterocycles
✍ Scribed by Frank T. Coppo; Maged M. Fawzi
- Publisher
- Journal of Heterocyclic Chemistry
- Year
- 1997
- Tongue
- English
- Weight
- 199 KB
- Volume
- 34
- Category
- Article
- ISSN
- 0022-152X
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✦ Synopsis
Abstract
The triethylamine‐catalyzed reaction of 4‐substituted ethyl 2‐acyl‐3‐amino‐6‐methylthieno[2,3‐b]pyridine‐4‐carboxylates IIIa‐h with 2,2,6‐trimethyl‐4__H__‐1,3‐dioxin‐4‐one IV gave 4‐substituted ethyl 3‐acetyl‐2‐hydroxy‐7‐methylthieno[2,3‐b:4,5‐b′]dipyridine‐9‐carboxylates Va‐h. Some of the thienodipyridines (V) reacted with excess IV to give 5‐substituted ethyl 3‐acetyl‐4,8‐dimethyl‐2‐oxo‐2H‐pyrano[2,3‐b]‐pyrido[3′,2′:4,5]thieno[2,3‐e]pyridine‐10‐carboxylates VI.
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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 malon