Effective Synthesis of Enantiopure [1,2,3]Triazolo[1,5-a]- and Pyrazolo[1,5-a]-pyrrolo[2,1-c][1,4]benzodiazepines by Diastereoselective Intramolecular Azide and Nitrilimine Cycloadditions

Gianluigi Broggini; Ivan De Marchi; Michela Martinelli; Giuseppe Paladino; Tullio Pilati; Alberto Terraneo

doi:10.1055/s-2005-869991

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Synthesis 2005(13): 2246-2252
DOI: 10.1055/s-2005-869991

PAPER

Effective Synthesis of Enantiopure [1,2,3]Triazolo[1,5-a]- and Pyrazolo[1,5-a]-pyrrolo[2,1-c][1,4]benzodiazepines by Diastereoselective Intramolecular Azide and Nitrilimine Cycloadditions

Gianluigi Broggini*^a, Ivan De Marchi^a, Michela Martinelli^a,b, Giuseppe Paladino^b, Tullio Pilati^c, Alberto Terraneo^d
^a Dipartimento di Scienze Chimiche e Ambientali, Università dell’Insubria, via Valleggio 11, 22100 Como, Italy
Fax: +39(031)2386449; e-Mail: gianluigi.broggini@uninsubria.it;
^b Istituto di Chimica Organica ‘A. Marchesini’, Facoltà di Farmacia, Università di Milano, via Venezian 21, 20133 Milano, Italy
^c Consiglio Nazionale delle Ricerche-Istituto di Scienze e Tecnologie Molecolari, via Golgi 19, 20133 Milano, Italy
^d Chorisis s.r.l., via Colombo 30/32, 22066 Mariano Comense (Como), Italy

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Publication History

Received 18 February 2005
Publication Date:
13 July 2005 (online)

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Abstract

The synthesis of new tetracyclic 1,4-benzodiazepinonic systems was performed in enantiopure form by totally diastereoselective intramolecular 1,3-dipolar cycloadditions. The absolute stereochemistry of the products was confirmed by X-ray crystallography and the enantiomeric purity was determined by using chiral HPLC.

Key words

azides - diastereoselectivity - fused-ring systems - nitrilimines - pyrrolo[2,1-c][1,4]benzodiazepines

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