Volume 21, Issue 1
Heterocyclic Compounds
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ChemInform Abstract: Pyrrolo(1,4)benzodiazepines. Part 4. Synthesis of E- and Z-5,11-Dioxo-11a-ethoxycarbonyl-2-ethylidene-1,2,3,10,11,11a-hexahydro-5H-pyrrolo(2,1-c)(1,4)benzodiazepine (VIIIa) and (VIIIb).

P. DE CAPRARIIS

P. DE CAPRARIIS

Dip. Chim. Farm. Tossicol., Univ. Napoli, 80131 Napoli, Italy

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G. DE MARTINO

G. DE MARTINO

Dip. Chim. Farm. Tossicol., Univ. Napoli, 80131 Napoli, Italy

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E. ABIGNENTE

E. ABIGNENTE

Dip. Chim. Farm. Tossicol., Univ. Napoli, 80131 Napoli, Italy

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P. AVARA

P. AVARA

Dip. Chim. Farm. Tossicol., Univ. Napoli, 80131 Napoli, Italy

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L. MAYOL

L. MAYOL

Dip. Chim. Farm. Tossicol., Univ. Napoli, 80131 Napoli, Italy

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First published: January 2, 1990

Abstract

The key intermediate (III) is obtained by NaBH4 reduction of the known precursor (I) using Py instead of THF as solvent (as tried previously what leads only to (II)).

ChemInform Abstract

The key intermediate (III) is obtained by NaBH4 reduction of the known precursor (I) using Py instead of THF as solvent (as tried previously what leads only to (II)). The E/Z isomers (VIII) prepared via (V) are separated to give (E)-(VIIIa), whose structure is similar to that of the antitumor antibiotic tomaymycin. When compound (X) is refluxed in P2O5/benzene, (VIIIa) is obtained as well, but in very low yield and in mixture with the vinyl derivative (VII).

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