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

HRID 976353Notes

Reaction equation

HRID 976353 reaction equation
O=[C:2]1[NH:8][C:7]2[S:9][CH:10]=[CH:11][C:6]=2[CH2:5][N:4]2[CH:12]=[CH:13][CH:14]=[C:3]12.[B].CSC>>[S:9]1[C:7]2[NH:8][CH2:2][C:3]3[N:4]([CH:12]=[CH:13][CH:14]=3)[CH2:5][C:6]=2[CH:11]=[CH:10]1

Participants

3

Reactant 2

HCID 9833925Boron, trihydro(thiobis(methane))-, (T-4)-HCID 110418649-oxo-9,10-dihydro-4H-pyrrolo[1,2-a]-thieno[2,3-e][1,4]diazepine

Product 1

HCID 218371599,10-dihydro-4H-pyrrolo[1,2-a]thieno[2,3-e][1,4]diazepine

Procedure

The synthesis of 9,10-dihydro-4H-furo[2,3-e]-pyrrolo[1,2-a][1,4]diazepin-9-one ##STR97## 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. ##STR98## The tricyclic 5,10-dihydro-4H-pyrazolo[5,1-c][1,4]benzo-diazepine ring system is reported by L. Cecchi and G. Filacchioni, J. Het. Chem., 20, 871 (1983); ##STR99## 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); ##STR100## and is reduced with boron-dimethylsulfide to give 9,10-dihydro-4H-pyrrolo [1,2-a]thieno [2,3-e][1,4]diazepine. ##STR101## Also reported by A. Daich and B. Decroix is 5-oxo-4,5-dihydropyrrolo [1,2-a]thieno[3,2-e][1,4]diazepine ##STR102## which is also reduced to give 4,10-dihydro-5H-pyrrolo-[1,2-a]thieno[3,2-e][1,4]diazepine ##STR103## Reported by B. Decroix and J. Morel, J. Het. Chem., 28, 81 (1991) are 5H-pyrrolo[1,2-a]thieno[3,2-e][1,4]diazepine; ##STR104## and 4H-pyrrolo[1,2-a]thieno[2,3-e][1,4]diazepine. The 10H-pyrrolo[1,2-a]thieno[3,4-e][1,4]diazepine is reported by A. Daich, J. Morel and B. Decroix, J, Heterocyclic Chem., 31, 341 (1994). Reduction by hydrogen-Pd/C or chemical reduction with reagents such as sodium cyanoborohydride and acetic acid gives the dihydro tricyclic heterocycles ##STR105## 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]benzo-diazepine is described. ##STR106##

Sources & evidence

ORD record
ord-c62a470df4b74e419459affc9d00741f
Source dataset
uspto-grants-1997_03
Patent number
US05612334

Reaction notes

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