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For recent uses of chloroacetic acid in Ugi reactions, see: a
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For recent uses of chloroacetic acid in Ugi reactions, see: (a) Marcaccini, S.; Pepino, R.; Cruz Pozo, M. Tetrahedron Lett. 2001, 42, 2727.
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33847027672
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For similar oxidations, see: ref. 10a,c and ref. 11
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For similar oxidations, see: ref. 10a,c and ref. 11.
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-
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55
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33847076199
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Typical Procedure (Given for 7c, Table 1, Anisaldehyde 1a (5 mmol, 608 μL, propargylamine (1 equiv, 343 μL, chloroacetic acid (1 equiv, 472 mg) and cyclohexyl isocyanide 2b (1 equiv, 622 μL) were added to MeOH (5 mL) and the mixture stirred overnight at r.t. The crude product was purified by flash chromatography using CH2Cl2 to give 1.41 g of 3b (70, To the chloro derivative 3b (3.2 mmol) in EtOH (3 mL) was added 4-picoline (2 equiv, 0.52 mL) and the mixture stirred at 50°C for 24 h. EtOH was evaporated, the crude product (1.6 mmol) was then added to 1-iodo-4-nitrobenzene (6b, 1.1 equiv, 876 mg) in a mixture THF-i-Pr2NH (1:1,6 mL, Then, Pd(OAc)2 (0.04 equiv, 28 mg, CuI (0.08 equiv, 48 mg) and PPh3 (0.08 equiv, 66 mg) were added and the mixture was stirred for 2 d. Extraction, evaporation and flash chromatography using Et2O-PE (50: 50) afford 590 mg of 7c
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5: 552.2373; found: 552.2385.
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(a) Dubowchik, G. M.; Michne, J. A.; Zuev, D. Bioorg. Med. Chem. Lett. 2004, 14, 3147.
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57
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0035808917
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(b) Kang, K. H.; Pae, A. N.; Choi, K.; Cho, Y. S.; Chung, B. Y.; Lee, J. E.; Jung, S. H.; Koh, H. Y.; Lee, H. Tetrahedron Lett. 2001, 42, 1057.
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Jung, S.H.7
Koh, H.Y.8
Lee, H.9
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58
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33847055457
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2O and filtration gave pyridinium 5 which was further treated as shown for 7c.
-
2O and filtration gave pyridinium 5 which was further treated as shown for 7c.
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