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Reactions of 2-Unsubstituted 1H-Imidazole 3-Oxides with Heterocumulenes and Dimethyl Acetylenedicarboxylate

✍ Scribed by Grzegorz Mlostoń; Tomasz Gendek; Heinz Heimgartner

Publisher
Elsevier Science
Year
2000
Tongue
French
Weight
145 KB
Volume
56
Category
Article
ISSN
0040-4020

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✦ Synopsis

AbstractÐReaction of 2-unsubstituted 1H-imidazole 3-oxides with isocyanates, isothiocyanates, and dimethyl acetylenedicarboxylate led to the formation of 2-functionalized imidazole derivatives. Stepwise reaction mechanisms via zwitterionic intermediates are proposed. The intermediate [312] cycloadducts stabilize via extrusion of COX or ring opening.

📜 SIMILAR VOLUMES

Straightforward Access to (Imidazol-2-yl
Straightforward Access to (Imidazol-2-yl)acetates by Reaction of 2-Unsubstituted Imidazole 3-Oxides with Dimethyl Acetylenedicarboxylate
✍ Grzegorz Mlostoń; Marcin Jasiński; Heinz Heimgartner 📂 Article 📅 2011 🏛 John Wiley and Sons 🌐 English ⚖ 177 KB 👁 1 views

## Abstract A new method for the preparation of 1,4,5‐trisubstituted (imidazol‐2‐yl)acetates, based on the reaction of the corresponding imidazole 3‐oxides with dimethyl acetylenedicarboxylate (DMAD) is described. Formation of the products is rationalized by a formal 1,3‐dipolar cycloaddition and s

ChemInform Abstract: Straightforward Acc
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The reaction of 1,4,5-trisubstituted 1H-imidazole-3-oxides 1 with 2,2-bis(trifluoromethyl)ethene-1,1dicarbonitrile (7, BTF) yielded the corresponding 1,3-dihydro-2H-imidazol-2-ones 10 and 2-(1,3-dihydro-2H-imidazol-2-ylidene)malononitriles 11, respectively, depending on the solvent used. In one exam