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Volumn , Issue 12, 2009, Pages 1921-1922

An efficient synthesis of functionalized 6,10-dioxo-6,10-dihydro-5H- pyrido[1,2-a]quinoxalines and 6,10-dioxo-6,10-dihydropyrido[2,1-c][1,4] benzoxazines

Author keywords

2 aminophenol; Acetylenic ester; Benzene 1,2 diamine; Malonyl dichloride; Pyrido 2,1 c 1,4 benzoxazine; Pyrido 1,2 a quinoxaline

Indexed keywords

6,10 DIOXO 6,10 DIHYDRO 5H PYRIDO[1,2 A]QUINOXALINE; 6,10 DIOXO 6,10 DIHYDROPYRIDO[2,1 C][1,4]BENZOXAZINE; ACETIC ACID DERIVATIVE; ALKYL GROUP; BENZOXAZINE DERIVATIVE; CARBOXYLIC ACID DERIVATIVE; MALONIC ACID DERIVATIVE; METHYL CHLORIDE; OXAZINE DERIVATIVE; PYRIDINE DERIVATIVE; QUINOXALINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 67651251420     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0029-1217542     Document Type: Article
Times cited : (20)

References (22)
  • 12
    • 0003989782 scopus 로고
    • 2nd ed, Wiley and Sons: New York
    • Gilchrist, T. L. Heterocyclic Chemistry, 2nd ed.; Wiley and Sons: New York, 1992, 272-276.
    • (1992) Heterocyclic Chemistry , pp. 272-276
    • Gilchrist, T.L.1
  • 17
    • 67651226621 scopus 로고    scopus 로고
    • General Procedure for the Synthesis of Compounds 4 To a suspension of 3 (2 mmol)18 in CH2Cl2 (10 mL) was added of malonyl dichloride (0.29 g, 2.1 mmol) at r.t. The reaction mixture was then stirred for 15 min. The formed precipitate was filtered off and washed with CH2Cl2 to afford the pure product. Compound 4a: pale yellow powder; mp 300-304°C (dec, yield 0.56 g (98, IR (KBr, νmax, 3450, 1729, 1693, 1655, 1490, 1418, 1365, 1306, 1258, 1106, 757 cm-1. 1H NMR (500 MHz, CDCl3, δ, 3.74 (3 H, s, OMe, 6.08 (1 H, s, CH, 7.12 (1 H, d, 3J, 7.8 Hz, CH, 7.20 (1 H, t, 3J, 7.9 Hz, CH, 7.30 (1 H, t, 3J, 8.0 Hz, CH, 9.19 (1 H, d, 3J, 7.8 Hz, CH, 11.76 (1 H, s, OH, 11.84 (1 H, s, NH) ppm. 13C NMR (125.7 MHz, CDCl3, δ, 52.6 (OMe, 102.9 (CH, 112.4 C
    • 5 (286.24): C, 58.75; H, 3.52; N, 9.79. Found: C, 58.60; H, 3.44; N, 9.65.
  • 18
    • 67651218362 scopus 로고    scopus 로고
    • Compound 4d: pale yellow powder; mp 298-300°C (dec, yield 0.55 g (97, IR (KBr) νmax, 3505, 1764, 1721, 1661, 1618, 1499, 1408, 1333, 1304, 1294, 1106, 759 cm-1. 1H NMR (500 MHz, CDCl3, δ, 3.79 (3 H, s, OMe, 6.12 (1 H, s, CH, 7.27 (1 H, t, 3J, 7.0 Hz, CH, 7.30 (1 H, d, 3J, 7.9 Hz, CH, 7.33 (1 H, t, 3J, 8.0 Hz, CH, 9.18 (1 H, d, 3J, 8.6 Hz, CH, 12.01 (1 H, s, OH) ppm.13C NMR (125.7 MHz, CDCl3, δ, 52.5 (OMe, 104.1 (CH, 114.8 (C, 116.8 (CH, 120.6 (CH, 123.1 (C, 124.3 (CH, 127.0 (CH, 127.9 (C, 141.1 (C, 154.2 (COH, 161.4 (CO, 161.5 (CO, 164.1 (CO2) ppm. Anal. Calcd, ) for C14H9NO6 287.22, C, 58.54; H, 3.16; N, 4.88. Found: C, 58.60; H, 3.14; N, 4.85
    • 6 (287.22): C, 58.54; H, 3.16; N, 4.88. Found: C, 58.60; H, 3.14; N, 4.85.
  • 19
    • 67651246398 scopus 로고    scopus 로고
    • Compound 4g: yellow powder; mp 298-301°C (dec, yield 0.58 g (98, IR (KBr) νmax, 3440, 1764, 1722, 1665, 1621, 1455, 1324, 1286, 1250, 1107, 765 cm-1. 1H NMR (500 MHz, CDCl 3, δ, 2.32 (3 H, s, Me, 3.78 (3 H, s, OMe, 6.10 (1 H, s, CH, 7.15 (1 H, d, 3J, 8.3 Hz, CH, 7.19 (1 H, d, 3J, 8.3 Hz, 9.03 (1 H, s, CH, 11.99 (1 H, s, OH) ppm. 13C NMR (125.7 MHz, CDCl3, δ, 20.9 (Me, 52.4 (OMe, 104.1 (CH, 114.8 (C, 116.5 (CH, 120.7 (CH, 122.6 (C, 127.4 (CH, 127.9 (C, 133.5 (C, 139.0 (C, 154.3 (C-OH, 161.3 (CO, 161.4 (CO, 164.1 (CO2) ppm. Anal. Calcd, ) for C15H11NO 6 301.25, C, 59.81; H, 3.68; N, 4.65. Found: C, 59.80; H, 3.65; N, 4.65. All other novel compounds isolated possessed spectroscopic and analytical data in keeping with their proposed structures
    • 6 (301.25): C, 59.81; H, 3.68; N, 4.65. Found: C, 59.80; H, 3.65; N, 4.65. All other novel compounds isolated possessed spectroscopic and analytical data in keeping with their proposed structures.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.