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Volumn , Issue 18, 2007, Pages 2815-2818

Novel and facile transformation of N,N-disubstituted glycylamides into corresponding cyanamides by using pentavalent iodine reagents in combination with tetraethylammonium bromide

Author keywords

Cyanamides; Dess Martin periodinane; Glycylamides; o iodoxybenzoic acid; Pentavalent iodine reagents; Tetraethylammonium bromide

Indexed keywords

AMIDE; CYANAMIDE; IODINE; REAGENT; TETRYLAMMONIUM BROMIDE;

EID: 36549081291     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-991093     Document Type: Article
Times cited : (38)

References (36)
  • 30
    • 36549053938 scopus 로고    scopus 로고
    • Kimura, I.; Muraoka, Y. JP 06 279 407, 1993.
    • (b) Kimura, I.; Muraoka, Y. JP 06 279 407, 1993.
  • 32
    • 36549044274 scopus 로고    scopus 로고
    • Preparation of N,N-Disubstituted Glycylamides 1, Procedure for 2-[4-(3-Trifluoromethylphenyl)piperizine-1-yl] Acetamide (1e, To a stirred solution of 4-(3-trifluoromethylphenyl)piperizine (3 g, 13 mmol) in EtOH (50 mL) were added K2CO3 (1.77 g, 13 mmol, 2-chloroacetamide (1.46 g, 15.6 mmol) and a catalytic amount of NaI (0.1 g, The resultant reaction mixture was refluxed for 6 h. After completion of reaction (monitoring by TLC) the reaction mixture was cooled, filtered, and the filtrate was evaporated under reduced pressure. The resultant residue was dissolved in EtOAc (200 mL) and washed with H2O (2 x 50 mL, brine, dried over anhyd Na2SO4, filtered, and concentrated under reduced pressure. The residue obtained was crystallized from MeOH-H2O to give the product as a white solid. Yield 80, mp 98-99°C. 1H NMR (60 MHz, CDCl3, δ, 3.29-3.31 (t, J, 3 Hz, 4 H, 3.41-3.43 t
    • -1.
  • 33
    • 36549023797 scopus 로고    scopus 로고
    • General Procedure for Cyanamides 2 To a stirred suspension of IBX (4.2 g, 15 mmol) in MeCN (50 mL) was added TEAB (3.15 g, 15 mmol) and the was mixture allowed to stir for 5 min. A yellow suspension was observed, to which N,N-disubstituted glycylamide (5 mmol) was added in one portion. The reaction mixture was heated to 60°C and held at this temperature until complete consumption of starting material (TLC, The reaction mixture was cooled and MeCN was removed under reduced pressure. The resultant residue was extracted with EtOAc (2 x 50 mL) and the organic layer was washed (1 x 30 mL) with 10% NaHSO3 solution, sat. Na2CO3, brine, dried over anhyd Na2SO4, filtered, and concentrated under reduced pressure to give crude cyanamide. Pure cyanamide was obtained after column chromatography (silica gel, mesh size 60-120; eluent EtOAc-hexane, 1:99, Piperidine-1-carbonitrile (2a) Oil.17a 1H NMR 60 MH
    • 2: C, 73.97; H, 6.84; N, 19.17. Found: C, 73.99; H, 6.87; N, 19.20.
  • 36
    • 36549007332 scopus 로고
    • DE 2106167
    • (b) Baker, J. A. DE 2106167, 1971.
    • (1971)
    • Baker, J.A.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.