메뉴 건너뛰기




Volumn , Issue 9, 2008, Pages 1279-1282

CAN-mediated oxidation of electron-deficient aryl and heteroaryl hydrazines and hydrazides

Author keywords

CAN; Deuteration; Hydrazides; Hydrazines; Oxidation

Indexed keywords

ACETONITRILE DERIVATIVE; CERIUM NITRATE; DEUTERIUM; HYDRAZIDE DERIVATIVE; HYDRAZINE DERIVATIVE; HYDROCARBON; METHANOL;

EID: 45749093449     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-1072749     Document Type: Article
Times cited : (15)

References (34)
  • 2
    • 34249898883 scopus 로고    scopus 로고
    • For reviews, see: a
    • For reviews, see: (a) Nair, V.; Deepthi, A. Chem. Rev. 2007, 107, 1862.
    • (2007) Chem. Rev , vol.107 , pp. 1862
    • Nair, V.1    Deepthi, A.2
  • 16
    • 45749147737 scopus 로고    scopus 로고
    • The products were analysed using MS spectrometry
    • The products were analysed using MS spectrometry.
  • 18
    • 45749086430 scopus 로고    scopus 로고
    • Typical Procedure: To a solution of CAN (2.193 g, 4 mmol) and 1,2-dibromotetrachloroethane (1.302 g, 4 mmol) in MeOH (5 mL) was added 2,4-dinitrophenylhydrazine (198 mg, 1 mmol) in one portion. The reaction mixture was stirred at r.t. for an additional 5 min, evaporated to dryness below 40°C, treated with H2O (10 mL) and extracted with CH 2Cl2 (5 x 10 mL, The organic phase was dried over anhyd Na2SO4 and concentrated under reduced pressure to give a mixture of products (2a:3Br:3Cl, 50:7.5:1, The mixture was purified by column chromatography (SiO2, EtOAc-light petroleum, 1:10, 2a: orange solid (134 mg, 80, Rf (light petroleum-EtOAc, 3:1) 0.34. 1H NMR (300 MHz, CDCl3, δ, 7.87 (t, J, 8.0 Hz, 1 H, 8.60 (dd, J, 2.0, 8.0 Hz, 2 H, 9.08 (t, J, 2.0 Hz, 1 H, 3Br: yellow oil (24 mg, 10, Rf light petr
    • 3): δ = 7.86 (d, J = 9.0 Hz, 1 H), 8.43 (dd, J = 5.5, 9.0 Hz, 1 H), 8.76 (d, J = 2.5 Hz, 1 H).
  • 22
    • 45749152063 scopus 로고    scopus 로고
    • General Procedure for the Oxidation of Hydrazines and Hydrazides: The hydrazine or hydrazide (1 mmol) was added at r.t. within a period of 10-15 min to a solution of CAN (4 mmol) in MeOH (5 mL, The reaction mixture was stirred at r.t. for an additional 10-40 min, evaporated to dryness below 40°C, treated with H2O (10 mL) and neutralised with NaHCO 3 (pH ca. 7, After extraction with CH2Cl2 (5 x 10 mL, the organic phase was dried over anhyd Na2SO4 and concentrated under reduced pressure to give dehydrazinated products 2. If necessary the products were purified by column chromatography on SiO 2. Products 2a-f, 8a and 8b were compared with the authentic samples. 2g: yellow solid; Rf (light petroleum-EtOAc, 5:3) 0.43; mp 69-72°C (MeCN, IR KBr, 3119, 1543, 1517, 1471, 1442, 1371, 1341, 1167, 1066, 1004, 849, 836, 762, 606, 566 cm -1
    • 3O: 161.0589; found: 161.0590.
  • 29
    • 45749116083 scopus 로고    scopus 로고
    • Representative Procedure for the Oxidation of Aryl Hydrazinecarboxylates 4a-c: An aryl hydrazine-carboxylate (1 mmol) was added at r.t. in one portion to a solution of CAN (2.1 mmol) in MeOH (5 mL, The reaction mixture was stirred at r.t. for an additional 5 min, evaporated to dryness below 40°C, treated with H2O (10 mL) and extracted with CH2Cl2 (5 x 10 mL, The organic phase was dried over anhyd Na2SO4 and concentrated under reduced pressure to give the pure products 5a-c. 5a: ref. 19. 5b: orange oil (213 mg, 94, Rf (light petroleum-EtOAc, 3:1) 0.59. IR (NaCl, 2985, 1758, 1572, 1503, 1389, 1368, 1296, 1245, 1211, 1165, 1029, 977, 889, 863, 826, 748 cm-1. 1H NMR (300 MHz, CDCl3, δ, 1.48 (t, J, 7.0 Hz, 3 H, 2.48 (s, 3 H, 4.53 (q, J, 7.0 Hz, 2 H, 7.41 (d, J, 8.0 Hz, 1 H, 7.79 (dd, J, 2.0, 8.0 Hz, 1 H, 7.93 d
    • 4: 243.0968; found: 243.00968.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.