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Synlett
Volumn , Issue 11, 2009, Pages 1795-1799
One-pot, three-component synthesis of a library of new pyrrolo[1,2-a] quinoline derivatives
Author keywords

1,3 dipolar cycloaddition; Multicomponent reaction; N ylide; Pyrrolo 1,2 a quinoline
Indexed keywords

2 BROMOACETOPHENONE DERIVATIVE; ACETOPHENONE DERIVATIVE; ACETYLENIC DIPOLAROPHILE DERIVATIVE; ELECTROPHILE; PROPYLENE OXIDE; PYRROLO (1,2 A) QUINOLINE DERIVATIVE; QUINOLINE DERIVATIVE; UNCLASSIFIED DRUG;
EID: 67649970688     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0029-1217367     Document Type: Article
Times cited : (64)
References (57)
  • 22
    • 67649945583 scopus 로고    scopus 로고
    • US Pat 20070293456
    • (f) Hayford, A.; Kaloko, J. US Pat 20070293456, 2007.
    • (2007)
    • Hayford, A.1    Kaloko, J.2
  • 26
    • 67649992086 scopus 로고    scopus 로고
    • Nakatsuka, M.; Shimamura, T. JP 2000277263, 2000.
    • (c) Nakatsuka, M.; Shimamura, T. JP 2000277263, 2000.
  • 41
    • 84890597202 scopus 로고    scopus 로고
    • Zhu, J, Bienayme, H, Eds, Wiley-VCH: Weinheim
    • (b) Multicomponent Reactions; Zhu, J.; Bienayme, H., Eds.; Wiley-VCH: Weinheim, 2005.
    • (2005) Multicomponent Reactions
  • 52
    • 67649933126 scopus 로고    scopus 로고
    • Synthesis of Pyrrolo[1,2-a]quinolines 4-33; General Procedure: Quinoline 1 (5 mmol, phenacyl bromide 2 (5 mmol) and non-symmetrical acetylene 3 (ethyl propiolate, 3-butyn-2-one or benzoylacetylene; 7 mmol) in 1,2-epoxypropane (40 mL) were stirred at room temperature for 30 h. The solvent was partly removed by evaporation, then methanol (10 mL) was added and the mixture was left overnight at room temperature. The solid was filtered, washed with a mixture of MeOH-Et 2O (1:1) and recrystallised from CHCl3-MeOH. Ethyl 1-(4-Methylbenzoyl)-7-methyl-pyrrolo[1,2-a]quinoline-3- carboxylate (19, Yellow crystals with mp 173-175°C were obtained by recrystallization from CHCl3-MeOH. Yield: 54, Anal. Calcd for C 24H21NO3: C, 77.61; H, 5.70; N, 3.77. Found: C, 77.91; H, 5.94; N, 3.98. FT-IR: 1617, 1654, 1704, 2976 cm-1. 1H NMR 300 MHz, CDCl
    • 2), 107.4 (C-3), 117.6 (C-4), 119.9 (C-9), 125.1, 128.0, 131.4, 135.9, 139.7 (C-1, C-3a, C-5a, C-9a, C-7), 128.3 (C-6), 129.4 (C-5), 128.6 (C-8), 129.1 (C-3′, C-5′), 129.9 (C-2), 130.2 (C-2′, C-6′), 135.1 (C-1′), 143.4 (C-4′), 164.1 (COO), 184.8 (COAr).
  • 53
    • 67649982649 scopus 로고    scopus 로고
    • Synthesis of Pyrrolo[1,2-a]quinolines 35-44; General Procedure: Quaternary salt 34a-j (5 mmol) and DMAD or DEAD (7 mmol) in 1,2-epoxypropane (40 mL) were stirred at room temperature for 24 h. The solvent was partly removed by evaporation, then methanol (10 mL) was added and the mixture was left overnight at room temperature. The solid was filtered, washed on filter with a mixture of MeOH-Et2O (1:1) and recrystallised from CHCl3-MeOH. Dimethyl 1-(3-Bromobenzoyl)-7-methylpyrrolo[1,2- a]quinoline-2,3-dicarboxylate (39, Yellow crystals with mp 192-194°C were obtained by recrystallization from MeOH-CHCl3. Yield: 44, Anal. Calcd for C23H18BrNO3: C, 63.32; H, 4.16; Br, 18.31; N, 3.21. Found: C, 63.44; H, 4.39; Br, 18.66; N, 3.56. FT-IR: 1617, 1654, 1704, 2976 cm-1. 1H NMR (300 MHz, CDCl3, d, 2.54 (s, 3 H, 7-Me, 3.50, 3.90 s, 6 H, 2-C
    • 3), 105.5 (C-3), 117.7 (C-4), 118.8 (C-9), 122.7 (C-3′), 125.3, 127.2, 128.8, 131.2, 135.7, 140.3 (C-1, C-3a, C-5a, C-9a, C-7, C-2), 128.4 (C-6), 128.5 (C-2′), 128.9 (C-5), 130.2 (C-5′), 130.4 (C-8), 132.7 (C-2′), 136.5 (C-4′), 139.5 (C-1′), 163.5, 165.1 (2 x COO), 185.7 (COAr).
  • 54
    • 67649951576 scopus 로고    scopus 로고
    • 000 = 392; R1 = 0.0428, wR2 = 0.1170. The CCDC deposition number: 718544.
    • 000 = 392; R1 = 0.0428, wR2 = 0.1170. The CCDC deposition number: 718544.
  • 55
    • 67649976348 scopus 로고    scopus 로고
    • 000 = 516; R1 = 0.0414, wR2 = 0.1132. The CCDC deposition number: 718545.
    • 000 = 516; R1 = 0.0414, wR2 = 0.1132. The CCDC deposition number: 718545.

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.