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Cycloaddition of haloketenes to imines: A convenient synthesis of functionally substituted β-lactams and 2-pyridones.

✍ Scribed by Fernando Duran; Léon Ghosez


Publisher
Elsevier Science
Year
1970
Tongue
French
Weight
200 KB
Volume
11
Category
Article
ISSN
0040-4039

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[2+2] Cycloaddition Reactions of Imines
✍ Giuseppe Cremonesi; Piero Dalla Croce; Concetta La Rosa 📂 Article 📅 2005 🏛 John Wiley and Sons 🌐 German ⚖ 190 KB

## Abstract Unsymmetric cyclic ketenes were generated from __N__‐acyl‐1,3‐thiazolidine‐2‐carboxylic acids **1a**–**c** by means of __Mukaiyama__'s reagent, and then reacted with imines **2a**–**c** to the new, isomeric spiro‐__β__‐lactams **3** and **4** __via__ [2+2] cycloaddition (__Staudinger__

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The d-manno-configured N-anisylated b-lactam 40, the b-lactam carboxylic acids 4 and 43, and the corresponding phosphonic-acid isosters 49 and 50 have been synthesized from d-glucose in 8 ± 10 steps, respectively. None of these compounds exhibited a significant inhibitory activity in vitro against t