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Volumn 6, Issue 2, 2000, Pages 321-326

Formal fusion of a pyrrole ring onto 2-pyridyl and 2-pyrimidyl cations: One-step gas-phase synthesis of indolizine and its derivatives

Author keywords

Cycloadditions; Heterocycles; Ion molecule reactions; Mass spectrometry

Indexed keywords

INDOLIZINE DERIVATIVE; PYRROLE DERIVATIVE;

EID: 0033984772     PISSN: 09476539     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3765(20000117)6:2<321::AID-CHEM321>3.0.CO;2-D     Document Type: Article
Times cited : (27)

References (40)
  • 1
    • 0000854468 scopus 로고
    • T. Kauffmann, Angew. Chem. 1965, 77, 557; Angew. Chem. Int. Ed. Engl. 1965, 4, 543.
    • (1965) Angew. Chem. , vol.77 , pp. 557
    • Kauffmann, T.1
  • 2
    • 84981830372 scopus 로고
    • T. Kauffmann, Angew. Chem. 1965, 77, 557; Angew. Chem. Int. Ed. Engl. 1965, 4, 543.
    • (1965) Angew. Chem. Int. Ed. Engl. , vol.4 , pp. 543
  • 29
    • 85037478625 scopus 로고    scopus 로고
    • note
    • The gaseous 4-pyrimidyl cation 5 appears to undergo facile "charge-induced ring opening" to form a more stable acyclic isomer, see ref. [4a].
  • 32
    • 0343470860 scopus 로고
    • b) T. Kauffmann, R. Wirthwein, Angew. Chem. 1971, 83, 21; Angew. Chem. Int. Ed. Engl. 1971, 10, 20.
    • (1971) Angew. Chem. Int. Ed. Engl. , vol.10 , pp. 20
  • 33
    • 85037472588 scopus 로고    scopus 로고
    • note
    • Under reaction conditions similar to those used for 1 and 2, the phenyl cation reacts with 1,3-butadiene and isoprene predominantly by proton transfer.
  • 34
    • 85037456205 scopus 로고    scopus 로고
    • note
    • For simplicity, only the formation of the ortho-cycloadduct is considered.
  • 36
    • 84993869502 scopus 로고
    • For the condensed-phase synthesis and properties of indolizines (pyrrolo[1,2-a]pyridines) and derivatives, see: a) T. Uchida, K. Matsumoto, Synthesis 1976, 209;
    • (1976) Synthesis , pp. 209
    • Uchida, T.1    Matsumoto, K.2
  • 38
    • 0347606904 scopus 로고
    • Indolizine (pyrrolo[1,2-a]pyridine) was synthesized according to the classic Scholtz reaction: M. Scholtz, Ber. 1912, 45, 734.
    • (1912) Ber. , vol.45 , pp. 734
    • Scholtz, M.1
  • 39
    • 85037466986 scopus 로고    scopus 로고
    • note
    • The minor differences observed in the relative abundances of fragments on comparison of Figure 6 and Figure 3 a probably result from the slightly different experimental setups and collision conditions (collision gas pressures and energies).
  • 40
    • 85037448009 scopus 로고    scopus 로고
    • note
    • Negligible activation barrier for ring-closure and reverse activation barrier for ring-opening, are assumed.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.