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Volumn , Issue 3, 2007, Pages 470-474

Simple and general synthesis of α-(p-nitroaryl) derivatives of alanine and serine

Author keywords

Amino acids; Arenes; Carbanions; Nucleophilic aromatic substitution

Indexed keywords

ALANINE DERIVATIVE; ALPHA(4 NITROARYL)ALANINE; ALPHA(4 NITROARYL)SERINE; AROMATIC NITRO COMPOUND; HYDROGEN; SERINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 33847384979     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-967952     Document Type: Article
Times cited : (17)

References (35)
  • 1
    • 33847419429 scopus 로고    scopus 로고
    • Summer Trainee from Higher Chemical College, Moscow, Russian Federation
    • Summer Trainee from Higher Chemical College, Moscow, Russian Federation.
  • 29
    • 33847398888 scopus 로고    scopus 로고
    • General Procedure for Oxidative Nucleophilic Substitution (Compounds 2a-8a and 2b-5b, To a stirred solution of t-BuOK (1.5 mmol) in THF (10 mL) cooled to -78°C under an argon atmosphere were added dropwise a solution of nitroarene (2 mmol) and the respective protected alanine ester (1 mmol) dissolved in DMF (2 mL, The resulting dark mixture was stirred at this temperature for 30 min and treated with DDQ (1.2 mmol) in THF (2 mL, The dark brown solution was stirred for 5 min at -78°C, then the mixture was allowed to reach r.t, ca. 30 min) and was then filtered trough a ca. 5 cm pad of silica gel and eluted subsequently with EtOAc-hexane. Evaporation of the solvents gave a residue that was purified by column chromatography (2b-5b) and recrystallized from EtOH or directly hydrolyzed (2a-8a, General Procedure for Oxidative Nucleophilic Substitution (Compounds 2c-11c, To a stirred solution of nitroarene 2 mmol, 4-carboethoxy-2-phenyl-2-oxazoline
    • 2O.
  • 35
    • 33847391330 scopus 로고    scopus 로고
    • With 2-chloronitrobenzene, the reaction was carried out at -78°C.
    • With 2-chloronitrobenzene, the reaction was carried out at -78°C.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.