1986
DOI: 10.1021/jo00360a014
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.alpha.-Nitroarylation of ketones and esters: an exceptionally facile synthesis of indoles, 2-indolinones and arylacetic acids

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Cited by 89 publications
(43 citation statements)
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“…110–111 °C. Analytical data for 2s were consistent with those previously reported . 1 H NMR (600 MHz, [D 6 ]DMSO): δ = 10.32 (br., 1 H), 7.25 (d, J = 7.4 Hz, 1 H), 7.16 (t, J = 7.7 Hz, 1 H), 6.93 (t, J = 8.0 Hz, 1 H), 6.85–6.76 (m, 1 H), 4.63 (s, 1 H), 3.54 (s, 2 H), 3.46 (s, 1 H), 1.99 (s, 1 H), 1.83 (s, 1 H) ppm.…”
Section: Methodssupporting
confidence: 89%
“…110–111 °C. Analytical data for 2s were consistent with those previously reported . 1 H NMR (600 MHz, [D 6 ]DMSO): δ = 10.32 (br., 1 H), 7.25 (d, J = 7.4 Hz, 1 H), 7.16 (t, J = 7.7 Hz, 1 H), 6.93 (t, J = 8.0 Hz, 1 H), 6.85–6.76 (m, 1 H), 4.63 (s, 1 H), 3.54 (s, 2 H), 3.46 (s, 1 H), 1.99 (s, 1 H), 1.83 (s, 1 H) ppm.…”
Section: Methodssupporting
confidence: 89%
“…As the nitro group on the benzene ring can be transformed into other important functional groups such as –NH 2 , –OH, –F, and –H, we proceeded to employ the above Meerwein cascade reaction followed by a reduction reaction under hydrogen with Pd/C as the catalyst to prepare o ‐(methoxycarbonyl)methyl anilines 4 . Anilines 4 were then heated at reflux in ethyl acetate in the presence of 4 Å molecular sieves to give oxindoles 5 in moderate total yields2a,9 (Scheme ).…”
Section: Resultsmentioning
confidence: 99%
“…141°C (lit. [21, 35] m.p. 140–141°C); IR (KBr): 3396 cm −1 (NH); 1 H NMR (CDCl 3 )[21]: δ 1.85–1.95 (m, 4H), 2.63–2.67 (m, 2H), 2.70–2.74 (m, 2H), 7.05 (dd, J = 7.5 Hz, 1.5 Hz, 1H), 7.17 (d, J = 7.5 Hz, 1H), 7.41 (d, J = 1.5 Hz, 1H), 7.65 (br s, 1H); 13 C NMR (CDCl 3 ): δ 20.7 (t), 23.0 (t), 23.1 (t), 23.2 (t), 110.0 (s), 111.2 (d), 117.3 (d), 120.9 (d), 124.7 (s), 128.9 (s), 133.9 (s), 135.7 (s).…”
Section: Methodsmentioning
confidence: 99%