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Volumn , Issue 13, 2007, Pages 2033-2036

Microwave-assisted reductive cyclization of N-allyl 2-nitroanilines: A new approach to substituted 1,2,3,4-tetrahydroquinoxalines

Author keywords

Cyclizations; Domino reactions; Ene reactions; Microwaves; Tetrahydroquinoxalines

Indexed keywords

2 ISOPROPENYL 1,2,3,4 TETRAHYDROQUINOXALINE; 3 ISOPROPENYL 1,2,3,4 TETRAHYDROQUINOXALINE; 4 ETHYL 3 ISOPROPENYL 1,2,3,4 TETRAHYDROQUINOXALINE; ANILINE DERIVATIVE; N ALLYL 2 NITROANILINE; QUINOXALINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 34548177308     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-984884     Document Type: Article
Times cited : (19)

References (32)
  • 20
    • 34548179572 scopus 로고    scopus 로고
    • Selected Data for 2a (Figure 3, Rf 0.40 (PE-EtOAc, 20:1, IR (ATR, 3376 (NH, 2952, 2854 (Me, CH2, 1691 (C=O, 1604, 1501 (C=C, 1435, 1382, 1372 (COO, 1232, 1211, 1146, 1061, COC, 900, 760, 741 cm-1. UV-Vis (EtOH, λmax (log ε, 307 (2.48, 253 (2.40, 220 (2.34) nm. 1H NMR (300 MHz, CDCl3, δ, 1.85 (s, 3 H, 3′-Me, 3.58 (dd, 2J, 12.3 Hz, 3J, 6.2 Hz, 1 H, 2-H, 3.81 (s, 3 H, OMe, 3.98 (dd, 3J, 3.4, 6.2 Hz, 1 H, 3-H, 4.02 (dd, 2J, 12.3 Hz, 3J, 3.3 Hz, 1 H, 2-H, 4.98 (br s, 1 H, 2′-H, 5.05 (br s, 1 H, 2′-H, 6.65 (dd, 3J, 8.0 Hz, 4J, 1.4 Hz, 1 H, 5-H, 6.70 (ddd, 3J, 7.4, 8.2 Hz, 4J, 1.5 Hz, 1 H, 7-H, 6.97 ddd, 3J, 7.4, 7.9 Hz, 4J, 1.4 Hz, 1 H, 6-H, 7.4
    • 2: C, 67.22; H, 6.94; N, 12.06. Found: C, 67.43; H, 7.01; N, 11.99. (Chemical Equation Presented) Figure 4
  • 21
    • 34548161117 scopus 로고    scopus 로고
    • Selected Data for 3a (Figure 4, Rf 0.59 (PE-EtOAc, 20:1, IR (ATR, 2980, 2958 (Me, CH2, 1702 (C=O, 1602, 1504 (C=C, 1438, 1375, 1344 (COO, 1217, 1190, 1145, 1062, COC, 899, 733 cm-1. UV-Vis (EtOH, λmax (log ε, 310 (2.49, 258 (2.41, 223 (2.35) nm. 1H NMR (300 MHz, CDCl 3, δ, 1.17 (t, 3J, 7.1 Hz, 3 H, 2″-Me, 1.80 (s, 3 H, 3′-Me, 3.15-3.27 (over-lapped, 2 H, 1″-CH2, 3.52 (dd, 2J, 13.1 Hz, 3J, 7.1 Hz, 1 H, 2-H, 3.76 (s, 3 H, OMe, 3.94 (t, 3J, 7.1 Hz, 1 H, 3-H, 4.37 (dd, 2J, 12.9 Hz, 3J, 7.1 Hz, 1 H, 2-H, 4.81 (br s, 1 H, 2′-H, 4.93 (br s, 1 H, 2′-H, 6.62 (dd, 3J, 8.1 Hz, 4J, 1.1 Hz, 1 H, 5-H, 6.75 ddd, 3J, 7.8, 8.1 Hz, 4J, 1.2 Hz
    • 2: 260.1525; found: 260.1507.
  • 25
    • 34548172684 scopus 로고    scopus 로고
    • Scheme 3 shows a mechanism involving a triplet nitrene. However, the occurrence of a singlet nitrene cannot be ruled out.
    • Scheme 3 shows a mechanism involving a triplet nitrene. However, the occurrence of a singlet nitrene cannot be ruled out.
  • 28
    • 34548174919 scopus 로고    scopus 로고
    • 4 and after concentration in vacuo was purified by flash chromatography on silica gel (PE-EtOAc, 20:1).
    • 4 and after concentration in vacuo was purified by flash chromatography on silica gel (PE-EtOAc, 20:1).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.