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Addition von Acetylendicarbonsäuredimethylester an Imidazole; Aminierung der Addukte: neue Synthesen von 3-(2-Imidazolyl)-2-pyridon-4,5-dicarbonsäureamiden und Pyrido[1,2-a]pyrazinen by Franz Troxler; Hans Peter Weber; André Jaunin; Hans-Rudolf Loosli is a Chemistry article available to read on EtoBox.

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## Abstract The reaction between dimethyl acetylene dicarboxylate and 2‐amino‐1‐methylimidazole affords dimethyl 2‐amino‐1‐methyl‐1,3‐diazepine‐5,6‐dicarboxylate in low yield. This 1:1 – adduct was formed by addition of the acetylenic compound to the enamine double bond of the imidazole ring followed by ring enlargement. On the other hand, 2:1 – adducts to the imine bond are isolated in moderate yield when dimethyl acetylene dicarboxylate is treated with either 1‐methyl‐2‐methylmercapto‐imidazole or 1‐methyl‐2‐methylmercapto‐imidazoline. These adducts behave differently on heating with ethylamine: the adduct of the imidazole series cyclizes to the pyridone **15** with concomittant loss of one carboxamide group whereas that of the imidazoline series forms a pyrido[1,2‐__a__]pyrazine derivative **20**, both in high yield. The possible reaction mechanisms are discussed. ^13^C–NMR.‐spectroscopy and X‐ray analysis were used in the determination of several structures.

Who reads Addition von Acetylendicarbonsäuredimethylester an Imidazole; Aminierung der Addukte: neue Synthesen von 3-(2-Imidazolyl)-2-pyridon-4,5-dicarbonsäureamiden und Pyrido[1,2-a]pyrazinen?

Author

Franz Troxler; Hans Peter Weber; André Jaunin; Hans-Rudolf Loosli

Publisher

John Wiley and Sons; Wiley (John Wiley & Sons); Wiley-Blackwell; Wiley (ISSN 0018-019X)

Published

1974

Language

DE

Field

Chemistry (Physical Sciences)