Voie d'acces preparative a un nouveau type de benzodiazepinones : les aryl-1 dihydro-3,4 5H benzodiazépines-2,3 ones-4

Wermuth, Camille‐Georges; Flammang, M.

doi:10.1016/s0040-4039(01)97423-4

Cited by 8 publications

(3 citation statements)

References 4 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…For the synthesis and pharmacological properties of the title compound, see: Flammang & Wermuth (1976); Wermuth & Flammang (1971). For related structures, see: Bruno et al (2001Bruno et al ( , 2003.…”

Section: Related Literaturementioning

confidence: 99%

See 1 more Smart Citation

1-Phenyl-3H-2,3-benzodiazepin-4(5H)-one

Daouda¹,

Bihel²,

Doumbia³

et al. 2012

Acta Cryst E

View full text Add to dashboard Cite

show abstract

Section: Related Literaturementioning

confidence: 99%

“…The solvent was removed and the white powder was recrystallized from ethanol to affford colorless crystals. The procedure was that reported in the literature (Flammang & Wermuth, 1976;Wermuth & Flammang, 1971).…”

Section: S2 Experimentalmentioning

confidence: 99%

1-Phenyl-3H-2,3-benzodiazepin-4(5H)-one

Daouda¹,

Bihel²,

Doumbia³

et al. 2012

Acta Cryst E

View full text Add to dashboard Cite

show abstract

“…The first representatives were prepared by Halford et al 1 by a procedure which was studied in detail by Wermuth and Flammang. [2][3][4] According to this, treatment of o-formyl-, o-acetyl-and o-aroylphenylacetic acids 2 with hydrazine or alkylhydrazines afforded 2,3-benzodiazepine-4-ones 1, beside 2-aminoisoquinolin-3(2H)-ones 3 as by-products (Scheme 1). The formation of the latter could be significantly reduced by optimization of reaction conditions.…”

mentioning

confidence: 99%

Practical Synthesis of Variously Substituted 2,3,4-Benzothiadiazepine 2,2-Dioxides

et al. 2022

View full text Add to dashboard Cite

The significant pharmacological activity of 2,3-benzodiazepine-4-ones led to an increased interest in this compound family. However, the literature of the closely related 2,3,4-benzothiadiazepine 2,2-dioxides is rather scarce. Earlier we elaborated a synthesis of 5-aryl congeners variously substituted at the aromatic ring. In the present study, a new synthetic route was investigated via highly versatile intermediates, to extend the reaction to a wider aromatic substitution pattern and to the preparation of 5-alkyl and 5-H derivatives. The essence of this approach is, starting from benzaldehyde acetals, acetophenone and benzophenone ketals, to synthesize ortho-formyl- and ortho-acyl-arylmethanesulfonyl chlorides, which are suitable precursors of the target compounds. The synthesis was implemented as follows: ortho-lithiation of the corresponding acetals and ketals and subsequent treatment with paraformaldehyde, or alternatively in two steps, with DMF or ethyl formate, followed by reduction with NaBH4, led to the corresponding hydroxymethyl derivatives. Reaction of these latter with methanesulfonyl chloride gave mesylates that were used to S-alkylate thiourea to afford S-alkylisothiouronium salts. The final steps of the synthesis were carried out in a telescoped reaction. Treatment of the S-alkylisothiouronium salts with N-chlorosuccinimide resulted in the corresponding arylmethanesulfonyl chlorides. Subsequent reaction with hydrazine hydrate followed by an acidic treatment gave 2,3,4-benzothiadiazepine 2,2-dioxides.

show abstract

References

1992

Chemistry of Heterocyclic Compounds: A Series of Monographs

View full text Add to dashboard Cite

Voie d'acces preparative a un nouveau type de benzodiazepinones : les aryl-1 dihydro-3,4 5H benzodiazépines-2,3 ones-4

Cited by 8 publications

References 4 publications

1-Phenyl-3H-2,3-benzodiazepin-4(5H)-one

1-Phenyl-3H-2,3-benzodiazepin-4(5H)-one

Practical Synthesis of Variously Substituted 2,3,4-Benzothiadiazepine 2,2-Dioxides

References

Contact Info

Product

Resources

About