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Volumn 51, Issue 25, 1995, Pages 7019-7034

Base-induced conversion of 5-aminothiazolium salts into substituted pyrroles and pyrrolines via 1,3-dipolar cycloadditions with electron-deficient alkynes and alkenes

Author keywords

[No Author keywords available]

Indexed keywords

PYRROLE DERIVATIVE; PYRROLINE DERIVATIVE; QUATERNARY AMMONIUM DERIVATIVE;

EID: 0029000152     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(95)00359-G     Document Type: Article
Times cited : (19)

References (36)
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    • Three-component cyclocondensations. Two methods for the efficient preparation of 5-aminothiazolium salts via the reaction of isocyanides either with dimethylthioformamide and imino chloro sulfides or benzaldimines and aryl chlorothioformates
    • (1993) The Journal of Organic Chemistry , vol.58 , pp. 6022-6029
    • Berrée1    Malvaut2    Marchand3    Morel4
  • 9
    • 77953502940 scopus 로고
    • 1.3-Dipolare Cycloadditionen, LVI. Eine bequeme Synthese vonN-substituierten Pyrrolen aus mesoionischen Oxazolonen und Alkinen
    • For recent review, see:
    • (1970) Chemische Berichte , vol.103 , pp. 2611-2624
    • Huisgen1    Gotthardt2    Bayer3    Schaefer4
  • 10
    • 84916492250 scopus 로고
    • The Synthesis of 1H-Pyrroles
    • R.A. Jones, Wiley, J, New York, part one
    • (1990) Pyrroles , vol.48 , pp. 165-168
    • Bean1
  • 14
    • 84916493108 scopus 로고    scopus 로고
    • 2 where we described the easy preparation of one pyrrole (4b) through the use of DMAD.
  • 15
    • 84916482124 scopus 로고    scopus 로고
    • 8 extrusion of isothiocyanate from mesoionic compounds was only related for the rearrangement of the 4-methyl-5-phenyl-1,3,4-thiadiazolium-2-anilide into the corresponding 1,3,4-triazolium-2-thiolate. This isomerisation proceeds via a cycloaddition with phenyl isothiocyanate: Ollis, W.D. ; Ramsden, C.A. J. Chem. Soc., Perkin Trans. I 1974, 633–638.
  • 17
  • 19
    • 84916524199 scopus 로고    scopus 로고
    • 3.
  • 20
    • 0001053434 scopus 로고
    • 1.3-Dipolare Cycloadditionen, XXX. Substituenteneffekte in den Kernresonanzspektren von 1.3-Diphenyl-Δ2-pyrazolinen und 3-Phenyl-Δ2-isoxazolinen
    • (1967) Chemische Berichte , vol.100 , pp. 1802-1813
    • Sustmann1    Huisgen2    Huber3
  • 21
    • 0342940606 scopus 로고
    • For instance, the mesoionic tetraphenylimidazolium-4-olate was found to be sluggishly reactive towards dimethyl fumarate and maleate giving succinimidopyrrolines via a process like (c), Scheme 5:
    • (1974) Tetrahedron Lett. , pp. 2169-2170
    • Singh1    Pande2
  • 27
    • 84916466377 scopus 로고
    • [3 + 2]-Cycloadditionen mesoionischer 1,3-Dithiolone an Ethylendicarbonsäure-Derivate und 1,2-Dibenzoylethylen
    • (1978) Chemische Berichte , vol.111 , pp. 3029-3036
    • Gotthardt1    Christl2
  • 29
    • 84916512284 scopus 로고    scopus 로고
    • 25


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.