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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1598147Generated: October 30, 2026

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

https://huagongshe.com/reaction/1598147

Reaction equation

Participants

RoleNameHCIDCharge
ReactantBoron, trihydro(thiobis(methane))-, (T-4)-HCID 9833925—
Reactant9-oxo-9,10-dihydro-4H-pyrrolo[1,2-a]-thieno[2,3-e][1,4]diazepineHCID 11041864—
Product9,10-dihydro-4H-pyrrolo[1,2-a]thieno[2,3-e][1,4]diazepineHCID 21837159—

Reaction Steps

The synthesis of 9,10-dihydro-4H-furo[2,3-e]-pyrrolo[1,2-a][1,4]diazepin-9-one ##STR171## 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. ##STR172## 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); ##STR173## 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 129, 360(1992); ##STR174## and is reduced with boron-dimethylsulfide to give 9,10-dihydro-4H-pyrrolo[1,2-a]thieno[2,3-e][1,4]diazepine. ##STR175## Also reported by A. Daich and B. Decroix is 5-oxo-4,5-dihydropyrrolo[1,2-a]thieno[3,2-e][1,4]diazepine ##STR176## which is also reduced to give 4,10-dihydro-5H-pyrrolo[1,2-a]thieno[3,2-e][1,4]diazepine ##STR177## 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; ##STR178## 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 ##STR179## 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. ##STR180##

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS05736540
Source datasetuspto-grants-1998_04
ORD IDord-4c5feafc858a4e97938296a27fbca0aa
Source noteuspto-grants-1998_04