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Volumn 10, Issue 14, 2008, Pages 3085-3088

Synthesis of 1(2H)-isoquinolones by the nickel-catalyzed denitrogenative alkyne insertion of 1,2,3-benzotriazin-4(3H)-ones

Author keywords

[No Author keywords available]

Indexed keywords

ALKYNE; BENZENE DERIVATIVE; ISOQUINOLINE DERIVATIVE; NICKEL; TRIAZINE DERIVATIVE;

EID: 52049100181     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol8010826     Document Type: Article
Times cited : (148)

References (38)
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    • For reviews, see: a
    • For reviews, see: (a) Varela, J. A.; Saá, C. Chem Rev. 2003, 103, 3787.
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    • Varela, J.A.1    Saá, C.2
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    • During the preparation of our manuscript, Matsubara and co-workers reported a nickel-catalyzed decarbonylative alkyne insertion of phthalimides: Kajita, Y.; Matsubara, S.; Kurahashi, T J. Am. Chem. Soc. 2008, 130, 6058.
    • (f) During the preparation of our manuscript, Matsubara and co-workers reported a nickel-catalyzed decarbonylative alkyne insertion of phthalimides: Kajita, Y.; Matsubara, S.; Kurahashi, T J. Am. Chem. Soc. 2008, 130, 6058.
  • 21
    • 37049141384 scopus 로고    scopus 로고
    • For thermolysis of 3-aryl-1,2,3-benzotriazin-4(3H)-ones, see: (a) Hey, D. H.; Rees, C. W.; Todd, A. R. J Chem. Soc. C 1968, 1028.
    • For thermolysis of 3-aryl-1,2,3-benzotriazin-4(3H)-ones, see: (a) Hey, D. H.; Rees, C. W.; Todd, A. R. J Chem. Soc. C 1968, 1028.
  • 27
    • 28244462079 scopus 로고    scopus 로고
    • For a previous example of alkyne insertion into a related seven-membered ring nickelacycle intermediate, see: Korivi, R. P, Cheng, C.-H. Org. Lett. 2005, 7, 5179. The authors assumed that a carbon-carbon triple bond can insert into both carbon-nickel and nitrogen-nickel linkages depending on alkynes. The regiochemistry observed in the present reaction using ethyl hex-2-ynoate (2h) suggests that a carbon-nickel linkage react with 2h. In the reaction of other alkynes such as terminal alkynes, however, insertion into a nitrogen-nickel linkage cannot be ruled out
    • For a previous example of alkyne insertion into a related seven-membered ring nickelacycle intermediate, see: Korivi, R. P.; Cheng, C.-H. Org. Lett. 2005, 7, 5179. The authors assumed that a carbon-carbon triple bond can insert into both carbon-nickel and nitrogen-nickel linkages depending on alkynes. The regiochemistry observed in the present reaction using ethyl hex-2-ynoate (2h) suggests that a carbon-nickel linkage react with 2h. In the reaction of other alkynes such as terminal alkynes, however, insertion into a nitrogen-nickel linkage cannot be ruled out.
  • 28
    • 59949084352 scopus 로고    scopus 로고
    • The benzotriazinone 1g was recovered.
    • The benzotriazinone 1g was recovered.
  • 29
    • 59949100534 scopus 로고    scopus 로고
    • See the Supporting Information for details
    • See the Supporting Information for details.
  • 30
    • 59949099908 scopus 로고    scopus 로고
    • Although a similar regiochemical preference was explained by assuming stabilization of a partial negative charge on the carbon α to nickel in ref 9b, the effect of the aryl substituent observed with the present reaction is inconsistent with this explanation. Further studies including a theoretical one are necessary for elucidation of the mechanistic and regiochemical issue
    • Although a similar regiochemical preference was explained by assuming stabilization of a partial negative charge on the carbon α to nickel in ref 9b, the effect of the aryl substituent observed with the present reaction is inconsistent with this explanation. Further studies including a theoretical one are necessary for elucidation of the mechanistic and regiochemical issue.
  • 31
    • 59949104314 scopus 로고    scopus 로고
    • 3 was self-oligomerization of 2h.
    • 3 was self-oligomerization of 2h.
  • 32
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    • For examples of the regioselective formation of α-boryl-substituted metalacycle intermediates, see: (a) Quntar, A. A. A, Srebnik, M. Org. Lett. 2004, 6, 4243
    • For examples of the regioselective formation of α-boryl-substituted metalacycle intermediates, see: (a) Quntar, A. A. A.; Srebnik, M. Org. Lett. 2004, 6, 4243.
  • 36
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    • For a similar stabilization by a silyl substituent, see
    • For a similar stabilization by a silyl substituent, see: Buchwald, S. L.; Nielsen, R. B. J. Am. Chem. Soc. 1989, 111, 2870.
    • (1989) J. Am. Chem. Soc , vol.111 , pp. 2870
    • Buchwald, S.L.1    Nielsen, R.B.2
  • 37
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    • 3 (85:15), DPPPen (92: 8), DPEphos (88:12), XANTPHOS (93:7).
    • 3 (85:15), DPPPen (92: 8), DPEphos (88:12), XANTPHOS (93:7).
  • 38
    • 59949094501 scopus 로고    scopus 로고
    • 3 as the ligand. For example, the reaction of 1-phenylprop-1-yne using dppf required heating at 80°C in toluene, giving inferior regioselectivity of 65:35.
    • 3 as the ligand. For example, the reaction of 1-phenylprop-1-yne using dppf required heating at 80°C in toluene, giving inferior regioselectivity of 65:35.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.