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Volumn 44, Issue 7, 2003, Pages 1461-1464

Conjugate additions of lithium dialkynylcuprates [(RC≡C)2CuLi] to activated chromones. Unexpected formation of the 6H-bis[1]benzopyrano[2,3-b:3′,4′-e]pyridine system

Author keywords

[No Author keywords available]

Indexed keywords

6H BIS[1]BENZOPYRANO[2,3 B:3',4' E]PYRIDINE; CHROMONE DERIVATIVE; COPPER DERIVATIVE; LITHIUM DERIVATIVE; NITRILE; PYRIDINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0037429097     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(02)02857-5     Document Type: Article
Times cited : (25)

References (27)
  • 16
    • 0012980158 scopus 로고    scopus 로고
    • 2O at -10 to -15°C for 30-60 min. Cuprates 1a and 1d give colourless to very pale yellow solutions, 1b is orange-yellow, whilst 1c formed a highly insoluble yellow-green solid.
    • 2O at -10 to -15°C for 30-60 min. Cuprates 1a and 1d give colourless to very pale yellow solutions, 1b is orange-yellow, whilst 1c formed a highly insoluble yellow-green solid.
  • 18
    • 0012924865 scopus 로고    scopus 로고
    • note
    • 3Si requires C, 66.2; H, 5.9%). Similarly, 1c provided 4c as an oil (21%) [bp (Kügelrohr) 155°C/0.15 mbar, mp 111.5-114°C]. Cuprate 1d provided 4d (90%) [bp (Kügelrohr) 150°C/0.1 mbar].
  • 19
    • 0012924084 scopus 로고    scopus 로고
    • note
    • Cuprate 1b and 2 provided 5Ab directly, after elution from silica (PhMe-EtOAc, 3:7) (50%, mp 158-159°C), whilst the crude product from 2 and 1c (silica, PhMe-EtOAc, 3:7) provided 5Ac (51%, mp 152-156.6°C).
  • 20
    • 0012967294 scopus 로고    scopus 로고
    • The absence of a cross peak for the alkene proton (δ 6.85) with that for H-2 (δ 6.60) is consistent with the (E) configuration for 5Aa. In 5Ba the (Z) stereochemistry is implicit since the alkene proton is shielded (δ 6.30) and shows a cross peak with the signal for H-2 at 6.10 ppm. The constitution of (Z)-5Ca follows from cross peaks for the -CHO group (δ 9.68) and the alkene proton (δ 6.75).
    • The absence of a cross peak for the alkene proton (δ 6.85) with that for H-2 (δ 6.60) is consistent with the (E) configuration for 5Aa. In 5Ba the (Z) stereochemistry is implicit since the alkene proton is shielded (δ 6.30) and shows a cross peak with the signal for H-2 at 6.10 ppm. The constitution of (Z)-5Ca follows from cross peaks for the -CHO group (δ 9.68) and the alkene proton (δ 6.75).
  • 21
    • 0013027476 scopus 로고    scopus 로고
    • note
    • 16 Crystallographic data (excluding structure factors) for the structure in this paper have been deposited with the Cambridge Crystallographic Data Centre as supplementary publication number no. CCDC 196356.
  • 23
    • 0012925612 scopus 로고
    • For 3-acetyl-2-methyl-5H-[1]benzopyrano[2,3-b]pyridin-5-one from 3 and acetylacetone, see:
    • For 3-acetyl-2-methyl-5H-[1]benzopyrano[2,3-b]pyridin-5-one from 3 and acetylacetone, see: Ghosh C.K. Synth. Commun. 8:1978;487.
    • (1978) Synth. Commun. , vol.8 , pp. 487
    • Ghosh, C.K.1
  • 24
    • 18844375618 scopus 로고    scopus 로고
    • For the pentacyclic bisbenzopyranopyridine system from condensation of 3 and chroman-4-ones, see:
    • For the pentacyclic bisbenzopyranopyridine system from condensation of 3 and chroman-4-ones, see: Reddy K., Venkat S.G., Rao A.V.S. Org. Prep. Proceed. Int. 28:1996;325.
    • (1996) Org. Prep. Proceed. Int. , vol.28 , pp. 325
    • Reddy, K.1    Venkat, S.G.2    Rao, A.V.S.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.