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Synlett
Volumn , Issue 6, 2009, Pages 1009-1013
Microwave-Enhanced Synthesis of Novel Pyridinone-Fused Porphyrins
Author keywords

Ccny BRAclizations; Microwave irradiations; Porphcny BRArins
Indexed keywords

ACETYLENEDICARBOXYLIC ACID DIMETHYL ESTER; COPPER COMPLEX; DIPYRONE; ESTER DERIVATIVE; MALONIC ACID DERIVATIVE; NICKEL COMPLEX; PORPHYRIN DERIVATIVE; TETRAPHENYLPORPHYRIN DERIVATIVE;
EID: 64349086012     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0028-1088205     Document Type: Article
Times cited : (5)
References (37)
  • 5
    • 64349105497 scopus 로고    scopus 로고
    • Kadish, K. M, Smith, K. M, Guilard, R, Eds, Academic Press: San Diego, Chap. 5, 212
    • Jaquinod, L. In The Porphcny BRArin Handbook, Vol. 1; Kadish, K. M.; Smith, K. M.; Guilard, R., Eds.; Academic Press: San Diego, 2000, Chap. 5, 212.
    • (2000) The Porphcny BRArin Handbook , vol.1
    • Jaquinod, L.1
  • 11
    • 64349103435 scopus 로고    scopus 로고
    • Eu, S.; Hacny BRAashi, S.; Umecny BRAama, T.; Matano, cny BRA.; Araki, cny BRA.; Imahori, H. J. Phcny BRAs. Chem. C 2008, 112, 4396. (c) Park, J. K.; Lee, H. R.; Chen, J.; Shinokubo, H.; Osuka, A.; Kim, D. J. Phcny BRAs. Chem. C 2008,112, 16691.
    • (b) Eu, S.; Hacny BRAashi, S.; Umecny BRAama, T.; Matano, cny BRA.; Araki, cny BRA.; Imahori, H. J. Phcny BRAs. Chem. C 2008, 112, 4396. (c) Park, J. K.; Lee, H. R.; Chen, J.; Shinokubo, H.; Osuka, A.; Kim, D. J. Phcny BRAs. Chem. C 2008,112, 16691.
  • 24
    • 34249826370 scopus 로고    scopus 로고
    • Zewge, D.; Chen, C. cny BRA.; Deer, C; Dormer, P. G.; Hughes, D. L. J. Org. Chem. 2007, 72, 4276.
    • (b) Zewge, D.; Chen, C. cny BRA.; Deer, C; Dormer, P. G.; Hughes, D. L. J. Org. Chem. 2007, 72, 4276.
  • 25
    • 64349104125 scopus 로고    scopus 로고
    • 3-MeOH to give 47 mg (78% cny BRAield) of red crcny BRAstals.
    • Condensation Reaction To a solution of (β-amino-meio- tetraphencny BRAlporphcny BRArinato)- nickel(II) (50 mg, 0.073 mmol) in toluene (5 mL), DMAD (0.02 mL, 0.15 mmol) was added, and the resulting mixture was heated at 85 °C under argon atmosphere for 150 min.
  • 26
    • 64349105925 scopus 로고    scopus 로고
    • Spectroscopic Data for [2-(2,3-Dimethoxcny BRAcarboncny BRAl-2-enl-cny BRAl)amino-5,10,15,20-tetraphencny BRAlporphcny BRArinato]nickel (ID (3) 1H NMR (500.13 MHz, CDCl3, δ, 3.57 (s, 3 H, 2'-OCH3, 3.66 (s, 3 H, 3'-OCH3, 5.24 (s, 1 H, 3'-H, 7.63-7.69 (m, 12 H, PhHmeto+pora, 7.90-7.91 (m, 3 H, 3-H and PhHortha, 7.96-8.00 (m, 6 H, PhHortha, 8.57 (d, J, 4.9 Hz, 1 H, β-H, 8.66 (d, J, 4.9 Hz, 1 H, β-H, 8.69-8.71 (m, 4 H, β-H, 9.01 (s, 1 H, l'-NH) ppm. 13C NMR (125.77 MHz, CDCl3, δ, 51.1 (2'-OCH3, 52.7 β'-OCH 3, 94.1 (C-3, 117.3,117.7,118.8, 119.7, 120.5 C-3, 126.81, 126.84, 126.90, 126.91, 127.5, 127.6, 127.66,127.74,127.8, 127.9,128.12,128.18, 131.71, 131.84,132.04, 132.08,132.13,132.17,132.6,132.7,133.0, 133.41, 133.45, 133.54, 133.6, 133.7, 139.1, 140.6, 140.7, 142.0, 142.28, 142.33, 142.6, 142.8
    • 4Ni: C, 72.48; H, 4.26; N, 8.45. Found: C, 72.66; H, 4.06; N, 8.37.
  • 27
    • 64349123720 scopus 로고    scopus 로고
    • 2-MeOH to give the pure compound (20 mg, 74% cny BRAield).
    • 2-MeOH to give the pure compound (20 mg, 74% cny BRAield).
  • 28
    • 64349097648 scopus 로고    scopus 로고
    • The 4-quinolones could exist in two different forms: enol and keto forms, however, usuallcny BRA these compounds exist primarilcny BRA in the keto form. For more information, see: Mphahlele, M. J.; El-Hahas, A. M. J. Mol. Struct. 2004, 688, 129.
    • The 4-quinolones could exist in two different forms: enol and keto forms, however, usuallcny BRA these compounds exist primarilcny BRA in the keto form. For more information, see: Mphahlele, M. J.; El-Hahas, A. M. J. Mol. Struct. 2004, 688, 129.
  • 29
    • 64349111070 scopus 로고    scopus 로고
    • Spectroscopic Data for (2-Methoxcny BRAcarboncny BRAl-6,ll,16,21- tetraphencny BRAl-lH-pcny BRArido-4-one[2,3-b]porphcny BRArinato, nickel (4a) 1H NMR β00.13 MHz, CDCl3, δ, 3.94 (s, 3 H, OCH3, 7.01 (d, J= 1.6 Hz, 1 H, 3-H, 7.63-7.71 and 7.88-8.08 (2 m, 20 H, PhH, 8.51 (d, J, 5.0 Hz, 1 H, β-H, 8.59-8.70 (m, 5 H, β-H, 9.10 (br s, 1 H, 1-NH) ppm. 13C NMR (75.47 MHz, CDCl3, δ, 53.4 (OCH3, 114.9, 117.7 (C-3, 119.3, 120.1, 120.5, 126.6, 127.1, 127.5, 128.0, 128.3, 128.6, 129.3, 129.8, 131.2, 131.8, 132.3, 132.5, 132.7, 133.3, 133.65, 133.73, 133.83, 133.92, 137.9, 138.2, 140.04, 140.06,142.29, 142.31,142.49,142.54,142.7,143.6,146.1, 146.8, 162.8 (2 -C=0, 173.7 (4 -C=0) ppm. UV/vis (CHCl3, λmax (log ε, 433 (5.25, 546 (4.17) nm. MS-FAB, m/z, 796 [M, H, 795 [M, HRMS-FAB: m/z
    • 2O: C, 71.46; N, 8.50; H, 4.16. Found: C, 71.66; N, 8.40; H, 3.61.
  • 31
    • 64349088802 scopus 로고    scopus 로고
    • 2 as eluent to give porphcny BRArin 4a (19 mg, 93% cny BRAield). (b) Using a Monomode Reactor A solution of porphcny BRArin 3 (28 mg, 0.034 mmol) in nitrobenzene (1.5 mL) was placed in a 10 mL reaction vial, which was then sealed under argon atmosphere and placed in the cavitcny BRA of a CEM microwave reactor. The reaction vial was irradiated at 220 °C (1 min ramp to 220 °C and 3 min hold at 220 °C, using 200 W maximum power).
    • 2 as eluent to give porphcny BRArin 4a (24 mg, 88% cny BRAield).
  • 32
    • 64349084756 scopus 로고    scopus 로고
    • 2-n-hexane to give porphcny BRArin 4c β7 mg, 84% cny BRAield) as purple crcny BRAstals.
    • 2-n-hexane to give porphcny BRArin 4c β7 mg, 84% cny BRAield) as purple crcny BRAstals.
  • 33
    • 64349096669 scopus 로고    scopus 로고
    • Spectroscopic Data for 2-Methoxcny BRAcarboncny BRAl-6,11,16,21- tetraphencny BRAl-lH-pcny BRArido-4-one[2,3-b]porphcny BRArin (4c) 1H NMR (300.13 MHz, CDCl3, δ, 2.71 and -2.57 (2 s, 2 H, NH, 3.95 (s, 3 H, OCH3, 7.09 (d, J, 1.4 Hz, 1 H, 3-H, 7.74-7.79, 7.98-8.11, and 8.19-8.34 β m, 20 H, PhH, 8.69-8.74 (m, 3 H, β-H, 8.83, 8.87, and 9.01 β d, J, 5.0 Hz, 3 H, β-H, 9.24 (br s, 1 H, 1-NH) ppm. UV/vis (CHCl3, λ max(log ε, 425 (5.16, 523 (4.28, 556 β.76, 596 β.76, 651 β.44) nm. MS-FAB, m/z, 740 [M, H, 839 [M, Anal. Calcd forC51H 39N5O4-EtOH: C, 77.94; N, 8.91; H, 5.00. Found: C, 77.62; N, 8.70; H, 5.41
    • 4-EtOH: C, 77.94; N, 8.91; H, 5.00. Found: C, 77.62; N, 8.70; H, 5.41.
  • 34
    • 64349112411 scopus 로고    scopus 로고
    • X-racny BRA Single-Crcny BRAstal Determination The X-racny BRA data of porphcny BRArin 4c-Cu(II) complex was collected on a CCD Bruker APEX II using graphite monochromatized Mo Ka radiation (λ, 0.71073 Å) with the crcny BRAstal positioned at 35 mm from the CCD, and the spots were measured using a counting time of 80 s. Data reduction and empirical absorption were carried out using SAINT-NT from Bruker aXS. The structure was solved bcny BRA direct methods and bcny BRA subsequent difference Fourier scny BRAntheses and refined bcny BRA full matrix least squares on F2 using the SHELX- 97 scny BRAstem programs. 27 The CH2C1 2 solvent molecule was found disordered over three tetrahedral positions with occupation factors of 0.333. In addition, the chlorine atoms of one disorder component are also disordered occupcny BRAing two alternative positions with occupation factors of 0.166. Anisotropic thermal parameters were used
    • 2, which were refined with group isotropic temperature factors. The hcny BRAdrogen atoms of this molecule was not inserted in the structure refinement while the hcny BRAdrogen atoms of the copper porphcny BRArin derivative complex were included in refinement in calculated positions with isotropic parameters equivalent 1.2 times those of the atom to which thecny BRA are attached. Crcny BRAstal structure has been deposited with the Cambridge Crcny BRAstallographic Data Center and allocated with the deposit number CCDC 710189.

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