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Volumn 12, Issue 6, 2010, Pages 1312-1315

Rhodium-catalyzed complete regioselective lntermolecular cross-cyclotrimerization of aryl ethynyl ethers and nitriles or isocyanates at room temperature

Author keywords

[No Author keywords available]

Indexed keywords

BINAP, 2 NAPHTHOL; BINAP, 2-NAPHTHOL; ETHER DERIVATIVE; ISOCYANIC ACID DERIVATIVE; NAPHTHALENE DERIVATIVE; NITRILE; ORGANOMETALLIC COMPOUND; PYRIDINE DERIVATIVE; PYRIDONE DERIVATIVE; RHODIUM;

EID: 77949831892     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol100182u     Document Type: Article
Times cited : (83)

References (27)
  • 3
    • 77949780397 scopus 로고    scopus 로고
    • JP 11263737, 1999
    • The zirconium-mediated cross-cyclotrimerization of ethyl ethynyl etiler and 3-hexyne was also reported as a patent; see: (b) Takahashi, T. JP 11263737, 1999; Chem. Abstr. 1999, 131, 228541.
    • (1999) Chem. Abstr. , vol.131 , pp. 228541
    • Takahashi, T.1
  • 7
    • 0001418998 scopus 로고
    • The homo-cyclotrimerization of di-tert-butoxyacetylene was reported; see: Semmelhack, M. F.; Park, J. Organometallics 1986, 5, 2550.
    • (1986) Organometallics , vol.5 , pp. 2550
    • Semmelhack, M.F.1    Park, J.2
  • 11
    • 77949817159 scopus 로고    scopus 로고
    • Other regioisomers were generated in <5% yields. A crosscyclotrimerization product of one molecule of 3a and two molecules of 4 was not detected at all.
    • Other regioisomers were generated in <5% yields. A crosscyclotrimerization product of one molecule of 3a and two molecules of 4 was not detected at all.
  • 12
    • 33644886020 scopus 로고    scopus 로고
    • Deiters and co-workers successfully overcame the regioselectivity problem in the cobalt-catalyzed intermolecular cross-cyclotrimerization of terminal, alkynes and nitriles by employing the solid-supported reaction system; see: Senaiar, R. S.; Young, D. D.; Deiters, A. Chem. Commun. 2006, 1313.
    • (2006) Chem. Commun. , pp. 1313
    • Senaiar, R.S.1    Young, D.D.2    Deiters, A.3
  • 14
    • 0142258960 scopus 로고    scopus 로고
    • The ruthenium-catalyzed regioselective cross-cyclotrimerization of methyl propiolate and electron-deficient nitriles leading to 2,3,6-trisubstituted pyridines was reported; see: (a) Varela, J. A.; Carlos, L.; Saá, C. J. Org. Chem. 2003, 68, 8595.
    • (2003) J. Org. Chem. , vol.68 , pp. 8595
    • Varela, J.A.1    Carlos, L.2    Saá, C.3
  • 18
    • 33748550638 scopus 로고    scopus 로고
    • For the rhodium-catalyzed intermolecular cross-cyclotrimerization of a terminal alkyne and an activated nitrile leading to two regioisomeric pyridines, see: Tanaka, K.; Suzuki, N.; Nishida, G. Eur. J. Org. Chem. 2006, 3917.
    • (2006) Eur. J. Org. Chem. , pp. 3917
    • Tanaka, K.1    Suzuki, N.2    Nishida, G.3
  • 19
    • 27144521700 scopus 로고    scopus 로고
    • Our research group reported the rhodium-catalyzed intermolecular cross-cyclotrimerization of terminal alkynes and isocyanates, but the regioselectivities vary depending on the alkynes used; see: Tanaka, K.; Wada, A.; Noguchi, K. Org Lett. 2005, 7, 4737.
    • (2005) Org Lett. , vol.7 , pp. 4737
    • Tanaka, K.1    Wada, A.2    Noguchi, K.3
  • 20
    • 55449099596 scopus 로고    scopus 로고
    • For recent reviews of the transition-metal-catalyzed cyclotrimerization for the synthesis of nitrogen heterocycles, see: (a) Varela, J. A.; Saá, C. Synlett 2008, 2571.
    • (2008) Synlett , pp. 2571
    • Varela, J.A.1    Saá, C.2
  • 26
    • 77949805954 scopus 로고    scopus 로고
    • Homo-cyclotrimerization products of 3a-e were generated as byproducts in the reactions of Tables 1-3.
    • Homo-cyclotrimerization products of 3a-e were generated as byproducts in the reactions of Tables 1-3.
  • 27
    • 77949863495 scopus 로고    scopus 로고
    • Although the slow addition of aryl ethynyl ether 3a to nitrile 6a or isocyanate 8a and the Rh catalyst over 30 min was also examined, the yields of the corresponding pyridine 7aa and 2-pyridone 9aa. were not increased.
    • Although the slow addition of aryl ethynyl ether 3a to nitrile 6a or isocyanate 8a and the Rh catalyst over 30 min was also examined, the yields of the corresponding pyridine 7aa and 2-pyridone 9aa. were not increased.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.