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Volumn , Issue 5, 2008, Pages 645-648

Expedient entry into 1,4-dihydroquinoxalines and quinoxalines via a novel variant of isocyanide-based MCR

Author keywords

Combinatorial chemistry; Dehydrogenations; Isocyanides; Multi component reactions; Quinoxalines

Indexed keywords

1,4 DIHYDROQUINOXALINE DERIVATIVE; BENZENE; QUINOXALINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 41349097979     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1032106     Document Type: Article
Times cited : (37)

References (22)
  • 10
    • 0348048827 scopus 로고    scopus 로고
    • One example of an aliphatic diamine participating in the intramolecular Ugi-type MCR has been reported in:Keung, W, Bakir, F, Patron, A. P, Rogers, D, Priest, C. D, Darmohusodo, V. Tetrahedron Lett. 2004, 45, 733
    • (a) One example of an aliphatic diamine participating in the intramolecular Ugi-type MCR has been reported in:Keung, W.; Bakir, F.; Patron, A. P.; Rogers, D.; Priest, C. D.; Darmohusodo, V. Tetrahedron Lett. 2004, 45, 733.
  • 11
    • 34547673707 scopus 로고    scopus 로고
    • An account of the use of ethylene diamines appeared in print when the present manuscript was in preparation: Kysil, V, Tkachenko, S, Khvat, A, Williams, C, Tsirulnikov, S, Churakova, M, Ivachtchenko, A. Tetrahedron Lett. 2007, 48, 6239
    • (b) An account of the use of ethylene diamines appeared in print when the present manuscript was in preparation: Kysil, V.; Tkachenko, S.; Khvat, A.; Williams, C.; Tsirulnikov, S.; Churakova, M.; Ivachtchenko, A. Tetrahedron Lett. 2007, 48, 6239.
  • 12
    • 41349090067 scopus 로고    scopus 로고
    • 1)-substituted benzimidazole, presumably formed from the oxidative cyclization of the intermediate aldimine. This observation is in accordance with our previous results, see ref. 11b. The unwanted benzimidazole formation could be minimized by thorough exclusion of air from the reaction medium.
    • 1)-substituted benzimidazole, presumably formed from the oxidative cyclization of the intermediate aldimine. This observation is in accordance with our previous results, see ref. 11b. The unwanted benzimidazole formation could be minimized by thorough exclusion of air from the reaction medium.
  • 14
    • 41349088580 scopus 로고    scopus 로고
    • Analytical Data for Selected Compounds Compound 5b: pale yellow solid, mp 156-157°C. 1H NMR (300 MHz, DMSO-d 6, δ, 7.50-7.59 (m, 7 H, 7.21-7.31 (m, 5 H, 6.34 (s, 1 H, NH, 3.64 (unresolved dd, 2 H, NHCH2, 2.93 (unresolved t, 2 H, NHCH2CH2, 2.37 (s, 3 H, 2.33 (s, 3 H, 13C NMR (75 MHz, DMSO-d6, δ, 150.0, 145.7, 140.3, 140.1, 139.6, 137.3, 135.5, 133.5, 129.6, 129.2 (two signals overlapped, 128.9, 128.8, 128.2, 126.4, 125.7, 42.9, 34.7, 20.2, 19.7. LCMS: m/z, 354 [M, 1, HRMS (EI, m/z calcd for C24H23N3: 353.4710; found: 353.4711. Compound 5g: grey solid, mp 203°C (decomp, 1H NMR (400 MHz, DMSO-d6, δ, 12.95 (brs, 1 H, COOH, 8.33 (d, J, 1.5 Hz, 1 H, 8.04 (dd, J, 8.6, 1.8 Hz, 1 H, 7.74 (m, 2 H, 7.64 (d, J, 8.6 Hz, 1 H, 7.55 m, 3 H
    • 3OS: 285.3703; found: 285.3703.
  • 15
    • 41349115877 scopus 로고    scopus 로고
    • Crystallographic data (excluding structure factors) for the structure 5b have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication number CCDC 671798. Copies of the data can be obtained free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: +44 (1223)336033 or email: deposit@ccdc.cam.ac.uk].
    • Crystallographic data (excluding structure factors) for the structure 5b have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication number CCDC 671798. Copies of the data can be obtained free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: +44 (1223)336033 or email: deposit@ccdc.cam.ac.uk].
  • 18
    • 41349120456 scopus 로고    scopus 로고
    • Characterization Data for 8 Brown oil. 1H NMR (300 MHz, DMSO-d6, δ, 8.79 (dd, J, 5.1, 1.8 Hz, 1 H, 8.50 (d, J, 7.3 Hz, 1 H, 7.73 (br s, 1 H, NH, 7.64 (m, 2 H, 7.53-7.59 (m, 4 H, 7.28-7.35 (m, 4 H, 7.22 (m, 1 H, 3.72 (dd, J, 14.2, 7.2 Hz, 2 H, NHCH2CH2, 2.98 (t, J, 7.2 Hz, 2 H, NHCH2CH2, 13C NMR (75 MHz, DMSO-d 6, δ, 158.4, 151.6, 147.0, 142.1, 136.7, 135.0, 134.9, 133.6, 130.1, 129.6, 128.5, 127.9, 127.2, 126.4, 125.8, 43.6, 35.2. LCMS: m/z, 327 [M, 1, HRMS EI, m/z calcd for C21H18N 4: 326.4044; found: 326.4047
    • 4: 326.4044; found: 326.4047.
  • 19
    • 41349098531 scopus 로고    scopus 로고
    • Characterization Data for 10 Off-white solid, mp 110-112°C. 1H NMR (300 MHz, DMSO-d6, δ, 7.24 (m, 3 H, 7.15 (m, 2 H, 6.86 (m, 1 H, 6.83 (m, 1 H, 6.72 (ddd, J, 7.6, 7.5, 1.6 Hz, 1 H, 6.53 (dd, J, 7.5, 1.6 Hz, 1 H, 5.47 (s, 1 H, dihydroquinaxoline-NH, 4.24 (br s, 1 H, NH-cycloC7H 13, 3.52 (s, 3 H, NCH3, 3.48 (m, 1 H, NHCH, 1.72-1.82 (m, 2 H, 1.44-1.67 (m, 8 H, 1.18-1.35 (m, 2 H, 13C NMR (75 MHz, DMSO-d6, δ, 149.8, 140.5, 132.1, 132.0, 128.8, 127.7, 126.4, 120.3, 119.9, 114.5, 113.0, 58.7, 53.4, 37.2, 36.6, 30.6, 28.3, 28.1, 24.7, 24.5. LCMS: m/z, 334 [M, 1, HRMS EI, m/z calcd for C22H27N3: 333.4806; found: 333.4803
    • 3: 333.4806; found: 333.4803.
  • 20
    • 41349097263 scopus 로고    scopus 로고
    • Characterization Data for 12 Brown viscous oil. 1H NMR (400 MHz, DMSO-d6, δ, 8.33 (dd, J, 4.9, 1.3 Hz, 1 H, 7.89 (dd, J, 7.6, 1.3 Hz, 1 H, 7.56 (m, 2 H, 7.51 (m, 3 H, 7.07 (dd, J, 4.9, 7.6 Hz, 1 H, 4.55 (t, J, 6.3 Hz, 2 H, MeOCH2, 3.65 (t, J, 6.3 Hz, 2 H, NHCH2, 3.30 (s, 3 H, OCH3, 3.24 (m, 1 H, NHCH, 1.44 (m, 2 H, 1.30-1.40 (m, 6 H, 1.21 (m, 2 H, 0.95 (m, 2 H, 13C NMR (75 MHz, DMSO-d 6, δ, 154.2, 149.0, 146.1, 139.8, 139.5, 136.1, 130.0, 129.0, 127.4, 117.1, 114.2, 68.3, 58.4, 58.0 (one signal obscured by DMSO sept, LCMS: m/z, 379 [M, 1, HRMS EI, m/z calcd for C23H 30N4O: 378.5218; found: 378.5221
    • 4O: 378.5218; found: 378.5221.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.