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Volumn 73, Issue 9, 2008, Pages 3658-3661

Electrophilic ipso-iodocyclization of N-(4-methylphenyl)propiolamides: Selective synthesis of 8-methyleneazaspiro[4,5]trienes

Author keywords

[No Author keywords available]

Indexed keywords

CYCLIZATION; SYNTHESIS (CHEMICAL);

EID: 43449133004     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo800328a     Document Type: Article
Times cited : (76)

References (46)
  • 6
  • 9
    • 43449083338 scopus 로고    scopus 로고
    • For selected papers on the synthesis of the spiro[4,5]decane skeleton by the intramolecular oxidative ipso-cyclization reactions of nitrenium ions, see: (a) Kawashima, T.; Naganuma, K.; Okazaki, R. Organometallics 1998, 17, 376-372.
    • For selected papers on the synthesis of the spiro[4,5]decane skeleton by the intramolecular oxidative ipso-cyclization reactions of nitrenium ions, see: (a) Kawashima, T.; Naganuma, K.; Okazaki, R. Organometallics 1998, 17, 376-372.
  • 18
    • 45549090574 scopus 로고    scopus 로고
    • We have also developed a general and selective protocol for the synthesis of spiro[4,5]trienyl acetates via an intramolecular electrophilic ipso-cyclization of N-arylpropiolamides with NIS and HOAc, in which no active substitutes at the para-position of the N-aryl ring were required; see: Tang, B.-X, Tang, D.-J, Tang, S, Yu, Q.-F, Zhang, Y.-H, Liang, Y, Zhong, P. Org. Lett. 2008, 10, 1063-1066
    • We have also developed a general and selective protocol for the synthesis of spiro[4,5]trienyl acetates via an intramolecular electrophilic ipso-cyclization of N-arylpropiolamides with NIS and HOAc, in which no active substitutes at the para-position of the N-aryl ring were required; see: Tang, B.-X.; Tang, D.-J.; Tang, S.; Yu, Q.-F.; Zhang, Y.-H.; Liang, Y.; Zhong, P. Org. Lett. 2008, 10, 1063-1066.
  • 19
    • 1542612770 scopus 로고    scopus 로고
    • For selected papers on the synthesis of the spiro[4,5]decane skeleton by the other ipso-cyclization methods, see: (a) Kende, A. S.; Koch, K. Tetrahedron Lett. 1986, 27, 6051-6054.
    • For selected papers on the synthesis of the spiro[4,5]decane skeleton by the other ipso-cyclization methods, see: (a) Kende, A. S.; Koch, K. Tetrahedron Lett. 1986, 27, 6051-6054.
  • 30
    • 15044349937 scopus 로고    scopus 로고
    • For selected recent papers on the electrophilic iodocyclizations of alkynes, see: a
    • For selected recent papers on the electrophilic iodocyclizations of alkynes, see: (a) Zhang, X.; Campo, M. A.; Yao, T.; Larock, R. C. Org. Lett. 2005, 7, 763-766.
    • (2005) Org. Lett , vol.7 , pp. 763-766
    • Zhang, X.1    Campo, M.A.2    Yao, T.3    Larock, R.C.4
  • 46
    • 43449085912 scopus 로고    scopus 로고
    • The two reactions of amine 1w and ester 1x were determined by GC-MS analysis. The results showed that no products were observed from the reaction of 1w, but 1,2-diiodoalkene (p-tolyl 2,3-diiodo-3- phenylacrylate) was detected from the reaction of 1x. Thus, we deduced that the electronic effect of the substrates plays a crucial role in the reaction
    • The two reactions of amine 1w and ester 1x were determined by GC-MS analysis. The results showed that no products were observed from the reaction of 1w, but 1,2-diiodoalkene (p-tolyl 2,3-diiodo-3- phenylacrylate) was detected from the reaction of 1x. Thus, we deduced that the electronic effect of the substrates plays a crucial role in the reaction.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.