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Volumn , Issue 9, 2009, Pages 1485-1493

A base-catalysed one-pot three-component coupling reaction leading to nitrosubstituted pyrroles

Author keywords

Heterocycles; Immobilized reagents; Multicomponent; Pyrroles

Indexed keywords

ETHYL CHLOROFORMATE; GOOD YIELD; HETEROCYCLES; IMMOBILIZED REAGENTS; ISOCYANIDE; MULTICOMPONENT; ONE POT; PYRROLES; THREE-COMPONENT COUPLING REACTION;

EID: 67650047702     PISSN: 00397881     EISSN: 1437210X     Source Type: Journal    
DOI: 10.1055/s-0028-1087991     Document Type: Article
Times cited : (27)

References (66)
  • 4
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    • Dolphin, D, Ed, Academic Press: New York
    • (d) The Porphyrins; Dolphin, D., Ed.; Academic Press: New York, 1977.
    • (1977) The Porphyrins
  • 23
    • 0031562377 scopus 로고    scopus 로고
    • and references cited therein. For a selection of the most generic methods see: a
    • For a selection of the most generic methods see: (a) De Kimpe, N.; Abbaspour, T. K.; Stevens, C.; De Cooman, P. Tetrahedron 1997, 53, 3693; and references cited therein.
    • (1997) Tetrahedron , vol.53 , pp. 3693
    • De Kimpe, N.1    Abbaspour, T.K.2    Stevens, C.3    De Cooman, P.4
  • 46
    • 34548357166 scopus 로고    scopus 로고
    • For selected reviews and application articles see: a
    • For selected reviews and application articles see: (a) Solinas, A.; Taddei, M. Synthesis 2007, 2409.
    • (2007) Synthesis , pp. 2409
    • Solinas, A.1    Taddei, M.2
  • 61
    • 67650062494 scopus 로고    scopus 로고
    • PS-BEMP refers to 2-tert-butylimino-2-diethylamino-1,3- dimethylperhydro-1,3,2-diazaphosphorine on polystyrene 2% DVB, loading 2.2 mmol/g. Commercially available from Aldrich Cat No. 20026-XXG where XX is the quantity in grams.
    • PS-BEMP refers to 2-tert-butylimino-2-diethylamino-1,3- dimethylperhydro-1,3,2-diazaphosphorine on polystyrene 2% DVB, loading 2.2 mmol/g. Commercially available from Aldrich Cat No. 20026-XXG where XX is the quantity in grams.
  • 62
    • 67650008837 scopus 로고    scopus 로고
    • PS-TBD refers to 1,5,7-triazabicyclo[4.4.0]dec-5-ene-polystyrene cross-linked with 2% DVB, loading 1.33 mmol/g. Commercially available from Biotage Cat. No. 800422.
    • PS-TBD refers to 1,5,7-triazabicyclo[4.4.0]dec-5-ene-polystyrene cross-linked with 2% DVB, loading 1.33 mmol/g. Commercially available from Biotage Cat. No. 800422.
  • 63
    • 67650042193 scopus 로고    scopus 로고
    • Available from Varian Inc. named as Bond Elut silica packed cartridges
    • Available from Varian Inc. named as Bond Elut silica packed cartridges.
  • 65
    • 67650018916 scopus 로고    scopus 로고
    • Experiments to try and exclude the possibility of excess ethyl chloroformate being responsible for the secondary products following addition to the nitrostyrene were conducted using sub-stoichiometric quantities to quench the original TosMIC anion. These reactions gave comparable crude mixtures accompanied by the components from the standard Barton-Zard condensation. The possibility that the TosMIC could still act as a leaving group and consequently as an ethyl formate transfer agent can still not be excluded
    • Experiments to try and exclude the possibility of excess ethyl chloroformate being responsible for the secondary products following addition to the nitrostyrene were conducted using sub-stoichiometric quantities to quench the original TosMIC anion. These reactions gave comparable crude mixtures accompanied by the components from the standard Barton-Zard condensation. The possibility that the TosMIC could still act as a leaving group and consequently as an ethyl formate transfer agent can still not be excluded.
  • 66
    • 67650025172 scopus 로고    scopus 로고
    • 1H NMR and X-ray analysis was used to confirm the structure.
    • 1H NMR and X-ray analysis was used to confirm the structure.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.