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Volumn , Issue 2, 2007, Pages 227-230

New indolizine template from the Ugi reaction

Author keywords

Indolizine; Isocyanide; Multicomponent reaction; Sonogashira coupling; Ugi reaction

Indexed keywords

AMINE; CHLOROACETIC ACID; INDOLIZINE DERIVATIVE; PROPARGYLAMINE; PYRIDINIUM DERIVATIVE; UNCLASSIFIED DRUG;

EID: 33847013752     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-968011     Document Type: Article
Times cited : (41)

References (58)
  • 1
    • 26844537872 scopus 로고    scopus 로고
    • For recent reviews, see: a
    • For recent reviews, see: (a) Banfi, L.; Riva, R. Org. React. 2005, 65, 1.
    • (2005) Org. React , vol.65 , pp. 1
    • Banfi, L.1    Riva, R.2
  • 52
    • 0035795047 scopus 로고    scopus 로고
    • For recent uses of chloroacetic acid in Ugi reactions, see: a
    • For recent uses of chloroacetic acid in Ugi reactions, see: (a) Marcaccini, S.; Pepino, R.; Cruz Pozo, M. Tetrahedron Lett. 2001, 42, 2727.
    • (2001) Tetrahedron Lett , vol.42 , pp. 2727
    • Marcaccini, S.1    Pepino, R.2    Cruz Pozo, M.3
  • 54
    • 33847027672 scopus 로고    scopus 로고
    • For similar oxidations, see: ref. 10a,c and ref. 11
    • For similar oxidations, see: ref. 10a,c and ref. 11.
  • 55
    • 33847076199 scopus 로고    scopus 로고
    • 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
    • 5: 552.2373; found: 552.2385.
  • 58
    • 33847055457 scopus 로고    scopus 로고
    • 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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