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Volumn 46, Issue 11, 2007, Pages 1869-1872

A remarkably simple and efficient benzannulation reaction

Author keywords

Cyclization; Fused ring systems; Microwave irradiation; Radical reactions; Synthetic methods

Indexed keywords

CYCLIZATION; FREE RADICALS; MICROWAVE IRRADIATION; SYNTHESIS (CHEMICAL);

EID: 34250837977     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200603416     Document Type: Article
Times cited : (57)

References (57)
  • 2
    • 33644506756 scopus 로고    scopus 로고
    • For recent references see: a
    • For recent references see: a) A. J. Clark, J. V. Geden, S. Thom, J. Org. Chem. 2006, 71, 1471-1479;
    • (2006) J. Org. Chem , vol.71 , pp. 1471-1479
    • Clark, A.J.1    Geden, J.V.2    Thom, S.3
  • 8
    • 0033618523 scopus 로고    scopus 로고
    • b) L. Yet, Tetrahedron 1999, 55, 9349-9403.
    • (1999) Tetrahedron , vol.55 , pp. 9349-9403
    • Yet, L.1
  • 16
    • 23444446027 scopus 로고    scopus 로고
    • For ATRC reactions leading to eight-membered rings see: a
    • For ATRC reactions leading to eight-membered rings see: a) D. Bertin, D. Gigmes, S. R. A. Marque, P. Tordo, Tetrahedron 2005, 61, 8752-8761;
    • (2005) Tetrahedron , vol.61 , pp. 8752-8761
    • Bertin, D.1    Gigmes, D.2    Marque, S.R.A.3    Tordo, P.4
  • 21
    • 34250899497 scopus 로고    scopus 로고
    • see also Ref, 6a];
    • b) see also Ref. [6a];
  • 23
    • 34250881314 scopus 로고
    • For pertinent discussions see: a
    • For pertinent discussions see: a) E. Lee, C. H. Yoon, T. H. Lee, J. Am. Chem. Soc. 1992, 114, 10 981-10 983;
    • (1992) J. Am. Chem. Soc , vol.114
    • Lee, E.1    Yoon, C.H.2    Lee, T.H.3
  • 26
    • 33645553942 scopus 로고    scopus 로고
    • For an overview see
    • For an overview see: H. Ishibashi, Chem. Rec. 2006, 6, 23-31.
    • (2006) Chem. Rec , vol.6 , pp. 23-31
    • Ishibashi, H.1
  • 30
    • 0001474120 scopus 로고    scopus 로고
    • Ligand 2 was prepared according to the method in: A. M. Magill, D. S. McGuinness, K. J. Cavell, G. J. P. Britovsek, V. C. Gibson, A. J. P. White, D. J. Williams, A. H. White, B. W. Skelton, J. Organomet. Chem. 2001, 617-618, 546-560. This particular catalyst system proved optimal for ATRC reactions leading to γ-butyrolactones and γ-butyrolactams J. Bull, Transfer Report, University of Manchester, 2005, We are currently screening the effectiveness of other catalyst systems in this reaction
    • Ligand 2 was prepared according to the method in: A. M. Magill, D. S. McGuinness, K. J. Cavell, G. J. P. Britovsek, V. C. Gibson, A. J. P. White, D. J. Williams, A. H. White, B. W. Skelton, J. Organomet. Chem. 2001, 617-618, 546-560. This particular catalyst system proved optimal for ATRC reactions leading to γ-butyrolactones and γ-butyrolactams (J. Bull, Transfer Report, University of Manchester, 2005). We are currently screening the effectiveness of other catalyst systems in this reaction.
  • 31
    • 34250890464 scopus 로고    scopus 로고
    • -1) readily undergoes hydrolytic ring opening upon exposure to moisture.
    • -1) readily undergoes hydrolytic ring opening upon exposure to moisture.
  • 32
    • 34250847392 scopus 로고    scopus 로고
    • 1H NMR spectroscopy indicates clean conversion into product. The low yield of 6 is due to mechanical losses incurred during removal of the toluene.
    • 1H NMR spectroscopy indicates clean conversion into product. The low yield of 6 is due to mechanical losses incurred during removal of the toluene.
  • 33
    • 0026509356 scopus 로고
    • For application to Kharasch reactions see: a
    • For application to Kharasch reactions see: a) F. Adámek, M. Hájek, Tetrahedron Lett. 1992, 33, 2039-2042;
    • (1992) Tetrahedron Lett , vol.33 , pp. 2039-2042
    • Adámek, F.1    Hájek, M.2
  • 34
    • 0035762929 scopus 로고    scopus 로고
    • ultrasound irradiation: M.-G. A. Shvekhgeimer, K. I. Kobrakov, D. M. Gafarov, Dokl. Akad. Nauk 2001, 377, 210-211.
    • b) ultrasound irradiation: M.-G. A. Shvekhgeimer, K. I. Kobrakov, D. M. Gafarov, Dokl. Akad. Nauk 2001, 377, 210-211.
  • 36
    • 4544238965 scopus 로고    scopus 로고
    • For the application of microwave technology to ATRP reactions see: a
    • For the application of microwave technology to ATRP reactions see: a) H. Zhang, U. S. Schubert, Macromol. Rapid Commun. 2004, 25, 1225-1230;
    • (2004) Macromol. Rapid Commun , vol.25 , pp. 1225-1230
    • Zhang, H.1    Schubert, U.S.2
  • 38
    • 34250901289 scopus 로고    scopus 로고
    • A Biotage Initiator microwave reactor (maximum power output of 300 W; operating frequency 2450 MHz) was used in the studies.
    • A Biotage Initiator microwave reactor (maximum power output of 300 W; operating frequency 2450 MHz) was used in the studies.
  • 39
  • 40
    • 27944506032 scopus 로고    scopus 로고
    • and references therein
    • A. M. Jacob, C. J. Moody, Tetrahedron Lett. 2005, 46, 8823-8825, and references therein.
    • (2005) Tetrahedron Lett , vol.46 , pp. 8823-8825
    • Jacob, A.M.1    Moody, C.J.2
  • 42
    • 3242780046 scopus 로고    scopus 로고
    • 2 from esters/lactones see: T. Mori, R. G. Weiss, Y. Inoue, J. Am. Chem. Soc. 2004, 126, 8961-8975, and references therein.
    • 2 from esters/lactones see: T. Mori, R. G. Weiss, Y. Inoue, J. Am. Chem. Soc. 2004, 126, 8961-8975, and references therein.
  • 45
    • 3843103610 scopus 로고    scopus 로고
    • For related (thermal) rearrangements see: a
    • For related (thermal) rearrangements see: a) U. Berg, H. Bladh, K. Mpampos, Org. Biomol. Chem. 2004, 2, 2125-2130;
    • (2004) Org. Biomol. Chem , vol.2 , pp. 2125-2130
    • Berg, U.1    Bladh, H.2    Mpampos, K.3
  • 52
    • 0034728627 scopus 로고    scopus 로고
    • It should be noted however that flash vacuum pyrolysis (FVP) techniques (T, ca. 1000°C) have also found application in the synthesis of polycyclic aromatic compounds: R. B. M. Ansems, L. T. Scott, J. Am. Chem. Soc. 2000, 122, 2719-2724
    • It should be noted however that flash vacuum pyrolysis (FVP) techniques (T = ca. 1000°C) have also found application in the synthesis of polycyclic aromatic compounds: R. B. M. Ansems, L. T. Scott, J. Am. Chem. Soc. 2000, 122, 2719-2724.
  • 54
    • 34250880517 scopus 로고    scopus 로고
    • Mechanistic studies are currently underway, the results of which will be reported in due course
    • Mechanistic studies are currently underway, the results of which will be reported in due course.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.