Intramolecular Azide Cycloaddition enroute to the New Pyrrolo[2,1-c][1,2,3] triazolo[1,5-a][1,4]benzodiazepine Skeleton

G.      Broggini; I.   De   Marchi; M.      Martinelli; G.      Paladino; A.      Penoni

doi:10.2174/1570178043400956

Abstract

The unknown pyrrolo[2,1-c][1,2,3]triazolo[1,5-a][1,4]benzodiazepin-8-one ring system has been synthesised starting from the N-Boc-L-proline methyl ester. The totally diastereoselective intramolecular 1,3- dipolar cycloaddition of the azide 9 constitutes the key step of the synthetic sequence.

Keywords: 1,4-benzodiazepin-5-ones, pyrrolo[2,1-c][1,4]benzodiazepin-5-ones, intramolecular cycloadditions, azides, diastereoselective reactions

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Letters in Organic Chemistry

Title: Intramolecular Azide Cycloaddition enroute to the New Pyrrolo[2,1-c][1,2,3] triazolo[1,5-a][1,4]benzodiazepine Skeleton

Volume: 1 Issue: 3

Author(s): G. Broggini, I. De Marchi, M. Martinelli, G. Paladino and A. Penoni

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Keywords: 1,4-benzodiazepin-5-ones, pyrrolo[2,1-c][1,4]benzodiazepin-5-ones, intramolecular cycloadditions, azides, diastereoselective reactions

Abstract: The unknown pyrrolo[2,1-c][1,2,3]triazolo[1,5-a][1,4]benzodiazepin-8-one ring system has been synthesised starting from the N-Boc-L-proline methyl ester. The totally diastereoselective intramolecular 1,3- dipolar cycloaddition of the azide 9 constitutes the key step of the synthetic sequence.

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Broggini G., Marchi De I., Martinelli M., Paladino G. and Penoni A., Intramolecular Azide Cycloaddition enroute to the New Pyrrolo[2,1-c][1,2,3] triazolo[1,5-a][1,4]benzodiazepine Skeleton, Letters in Organic Chemistry 2004; 1 (3) . https://dx.doi.org/10.2174/1570178043400956