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Volumn , Issue 6, 2009, Pages 965-967

β-nitroacrylates as key starting materials for the uncatalysed one-pot synthesis of polyfunctionalized dihydroquinoxalinone derivatives, via an anti-Michael reaction

Author keywords

Nitroacrylates; Anti Michael reaction; Quinoxalinones; Uncatalysed

Indexed keywords

1,2 PHENYLENEDIAMINE; ACRYLIC ACID DERIVATIVE; QUINOXALINE DERIVATIVE;

EID: 63849248232     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0028-1088197     Document Type: Article
Times cited : (36)

References (36)
  • 1
    • 84944048121 scopus 로고
    • Review: a, Katritzky, A. R, Rees, C. W, Eds, Pergamon: Oxford
    • Review: (a) Porter, A. E. In Comprehensive Heterocyclic Chemistry, Vol 3; Katritzky, A. R.; Rees, C. W., Eds.; Pergamon: Oxford, 1984, 157.
    • (1984) Comprehensive Heterocyclic Chemistry , vol.3 , pp. 157
    • Porter, A.E.1
  • 2
    • 33750059386 scopus 로고    scopus 로고
    • Katritzki, A. R, Rees, C. W, Scriven, E. F. V, Eds, Pergamon: Oxford
    • (b) Sato, N. In Comprehensive Heterocyclic Chemistry II, Vol. 6; Katritzki, A. R.; Rees, C. W.; Scriven, E. F. V., Eds.; Pergamon: Oxford, 1996, 233.
    • (1996) Comprehensive Heterocyclic Chemistry II , vol.6 , pp. 233
    • Sato, N.1
  • 36
    • 63849284546 scopus 로고    scopus 로고
    • Typical Procedure for the Conjugate Addition of Active Methylene 5 to β-Nitroacrylates 1 β-Nitroacrylate 2(1 mmol) and o-phenylenediamine 1 (1.25 mmol) were dissolved in EtOAc (2 mL) and mixed at r.t, with magnetic stirring, for 2 h. Then, acetone (2 mL, in order to increase the solubility of 4) and 0.8 g of SiO2 (Silica Gel 60, 0,040-0,063 mm, 230-400 mesh ASTM, Merck, were added and the mixture was stirred for 5 min. Finally, the solvent was removed under vacuum and the crude product (adsorbed on SiO2) was charged onto a chromatography column (cyclohexane-EtOAc) allowing the pure products 4. Spectroscopic Data for Representative Compounds Compound 4b (diastereomeric mixture, yellow solid. IR (KBr, v, 1362, 1546, 1686, 3049, 3414 cm-1. 1H NMR (400 MHz, acetone, δ, 0.95 (t, 3 H, J, 7.3 Hz, 1.88-2.02 (m, 1 H, 2.07-2.25 (m, 1 H, 4.39 dd, 0.27 H, J= 3.4, 6
    • 5 (307.30): C, 54.72; H, 5.58; N, 13.67. Found: C, 54.36; H, 5.31; N, 13.83.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.