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HRID 3485Erstellt: 25. Oktober 2026

Boron, trihydro(thiobis(methane))-, (T-4)- → 9,10-dihydro-4H-pyrrolo[1,2-a]thieno[2,3-e][1,4]diazepine

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Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
EduktBoron, trihydro(thiobis(methane))-, (T-4)-HCID 9833925—
Edukt9-oxo-9,10-dihydro-4H-pyrrolo[1,2-a]-thieno[2,3-e][1,4]diazepineHCID 11041864—
Produkt9,10-dihydro-4H-pyrrolo[1,2-a]thieno[2,3-e][1,4]diazepineHCID 21837159—

Reaktionsschritte

The synthesis of 9,10-dihydro-4H-furo[2,3-e]pyrrolo[1,2-a][1,4]diazepin-9-one ##STR143## is reported by F. Povazunec, B. Decroix and J. Morel, J. Het. Chem. 29, 1507(1992) and is reduced to give the tricyclic heterocycle 9,10-dihydro-4H-furo[2,3-e]pyrrolo[1,2-a][1,4]diazepine. ##STR144## The tricyclic 5,10-dihydro-4H-pyrazolo[5,1-c][1,4]benzodiazepine ring system is reported by L. Cecchi and G. Filacchioni, J. Het. Chem., 20, 871(1983); ##STR145## The synthesis of 9-oxo-9,10-dihydro-4H-pyrrolo[1,2-a]thieno[2,3-e][1,4]diazepine is reported by A. Daich and B. Decroix, Bull. Soc. Chim. Fr 12, 360(1992); ##STR146## and is reduced with boron-dimethylsulfide to give 9,10-dihydro-4H-pyrrolo[1,2-a]thieno[2,3-e][1,4]diazepine. ##STR147## Also reported by A. Daich and B. Decroix is 5-oxo-4,5-dihydropyrrolo[1,2-a]thieno[3,2-e][1,4]diazepine ##STR148## which is also reduced to give 4,10-dihydro-5H-pyrrolo[1,2-a]thieno[3,2-e][1,4]diazepine ##STR149## Reported by B. Decroix and J. Morel, J. Het. Chem., 28, 81(1991) are pyrrolo[1,2-a]thieno[3,2-e][1,4]diazepine; ##STR150## and pyrrolo[1,2-a]thieno[2,3-e][1,4]diazepine. Reduction by hydrogen-Pd/c or chemical reduction with reagents such as sodium cyanoborohydride and acetic acid gives the dihydro tricyclic heterocycles ##STR151## The synthesis of the tricyclic 1,5-benzodiazepine ring system, 6,7-dihydro-5H-pyrrolo[1,2-a][1,5]benzodiazepine, has been reported by F. Chimenti, S. Vomero, R. Giuliano and M. Artico, IL Farmaco, Ed. Sc., 32, 339(1977). Annelated 1,5-benzodiazepines containing five membered rings have been reviewed by A. Chimirri, R. Gitto, S. Grasso, A. M. Monforte, G. Romeo and M. Zappala, Heterocycles, 36, No. 3, 604(1993), and the ring system 6,7-dihydro-5H-pyrrolo[1,2-a][1,5]benzodiazepine is described. ##STR152##

Herkunft & Nachweise

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS05733905
Quelldatensatzuspto-grants-1998_03
ORD IDord-d120900bcd1d4b5b9cba3cd8953676b0
Quellennotizuspto-grants-1998_03