75. The search for chemotherapeutic amidines. Part XII. NN′-di(amidinophenyl)amidines

Crundwell, E.

doi:10.1039/jr9560000368

Cited by 7 publications

(2 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…2-Bromoanilide substrates for oxindole synthesis ( 9 , 12 , 14 , 16 , 18 , 20 , 22 , 24 ) were prepared from 2-bromoanilines by coupling to the appropriate acid chloride followed by N -alkylation of the resulting amide. 4-Amino-3-bromoanisole was prepared from 3-bromophenol by literature methods. , 4-Amino-3-bromobenzonitrile was prepared by the previously reported bromination of 4-aminobenzonitrile . Naphthalene was used as a standard in quantitative GC experiments using response factors determined from isolated products.…”

Section: Methodsmentioning

confidence: 99%

“…55,56 4-Amino-3-bromobenzonitrile was prepared by the previously reported bromination of 4-aminobenzonitrile. 57 Naphthalene was used as a standard in quantitative GC experiments using response factors determined from isolated products. 1 H and 13 C NMR data are reported in ppm from TMS and were referenced to residual solvent protons or internal TMS.…”

Section: Methodsmentioning

confidence: 99%

See 1 more Smart Citation

Palladium-Catalyzed Inter- and Intramolecular α-Arylation of Amides. Application of Intramolecular Amide Arylation to the Synthesis of Oxindoles

1998

View full text Add to dashboard Cite

2A palladium-catalyzed α-arylation of amides is reported. Intermolecular arylation of N,N-dimethylamides and lactams occurs using aryl halides, silylamide base, and a palladium catalyst. Intramolecular arylation of N-(2-halophenyl)amides occurs using alkoxide base and a palladium catalyst. The palladium catalyst was formed in situ from Pd(dba)2 (dba = trans,trans-dibenzylidene acetone) and BINAP (2,2‘-bis(diphenylphosphino)-1,1‘-binaphthalene). Although the intermolecular arylation of amides is less general than that reported previously for ketones, unfunctionalized and electron-rich aryl halides gave α-arylamides in 48−75% yield and N-methyl-α-phenylpyrrolidinone in 49% yield. These reactions provided the highest yields yet reported for regioselective amide arylations. Intramolecular amide arylation of 2-bromoanilides gave oxindoles in 52−82% yield. Mono- and disubstituted acetanilides gave 1,3-di- and 1,3,3-trisubstituted oxindoles. The use of dioxane, rather than THF, solvent was important for some of the amide arylations.

show abstract

Section: Methodsmentioning

confidence: 99%