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Reaction of 5-substituted-2-amino-2-oxazolines with ethoxycarbonyl isocyanate. A route to 2,3,6,7-tetrahydro-4H-oxazolo[3,2-a]-1,3,5-triazine-2,4-diones

✍ Scribed by Ouro Adetchessi; Daniel Desor; Isabelle Forfar; Christian Jarry; Jean Michel Leger; Michel Laguerre; Alain Carpy

Publisher
Journal of Heterocyclic Chemistry
Year
1997
Tongue
English
Weight
504 KB
Volume
34
Category
Article
ISSN
0022-152X

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✦ Synopsis

Abstract

The reaction of 2‐amino‐2‐oxazolines with ethoxycarbonyl isocyanate was investigated in order to access to fused 1,3,5‐triazine‐2,4‐diones with a potential 5‐HT~2~ antagonist activity. The reaction leads to 2,3,6,7‐tetrahydro‐4__H__‐oxazolo[3,2‐a]‐1,3,5‐triazine‐2,4‐diones and to 1‐carbethoxy‐3‐(2‐iminooxazolidine)ureas. During the carbamoylation the regioselectivity seems to be related to the strong nucleophilic character of the endo nitrogen atom of 2‐amino‐2‐oxazolines. The structures of two compounds were studied by X‐ray crystallography. N‐Substituted compounds have been prepared by alkylation of the 2,3,6,7‐tetrahydro‐7‐phenoxymethyl‐4__H__‐oxazolo[3,2‐a]‐1,3,5‐triazine‐2,4‐dione.

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An easy route to 2-substituted-2,3-dihyd
An easy route to 2-substituted-2,3-dihydro-5(7)H-oxazolo[3,2-a]pyrimidin-5-ones and 7-ones starting from the corresponding 2-amino-2-oxazolines
✍ I. Forfar; J. Guillon; S. Massip; J.-M. Léger; C. Jarry; J.-P. Fayet 📂 Article 📅 2001 🏛 Journal of Heterocyclic Chemistry 🌐 English ⚖ 56 KB

## Abstract The isomeric 2‐substituted‐7(5)‐methyl‐2,3‐dihydro‐5(7)__H__‐oxazolo[3,2‐__a__]pyrimidin‐5‐ones **3a‐b** and 7‐ones **2a‐b,7a** were synthesized by cyclocondensation from the 5‐substituted‐2‐amino‐2‐oxazolines **1a‐b** with biselectrophiles. In boiling ethanol, the reaction of **1a‐b**