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Volumn 132, Issue 12, 2010, Pages 4381-4387

Radical migration of substituents of aryl groups on quinazolinones derived from N-Acyl cyanamides

Author keywords

[No Author keywords available]

Indexed keywords

ARYL GROUP; DOMINO PROCESS; HOMOLYTIC SUBSTITUTION; QUINAZOLINONES; REACTION CONDITIONS; TRIFLUOROMETHYL;

EID: 77950284297     PISSN: 00027863     EISSN: 15205126     Source Type: Journal    
DOI: 10.1021/ja910653k     Document Type: Article
Times cited : (86)

References (53)
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    • (d) Radicals in Organic Synthesis; Renaud, P., Sibi, M. P., Eds.; Wiley-VCH: Weinheim, Germany, 2001; Vol.2.
    • (2001) Radicals in Organic Synthesis , vol.2
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    • (e) Renaud, P. Chimia 2001, 55, 1045-1048.
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    • 0002523168 scopus 로고    scopus 로고
    • Renaud, P., Sibi, M. P., Eds.; Wiley-VCH: Weinheim, Germay
    • (a) Studer, A.; Bossart, M. Radicals in Organic Synthesis; Renaud, P., Sibi, M. P., Eds.; Wiley-VCH: Weinheim, Germay, 2001; Vol.2, pp 62-80.
    • (2001) Radicals in Organic Synthesis , vol.2 , pp. 62-80
    • Studer, A.1    Bossart, M.2
  • 22
  • 29
    • 27644476270 scopus 로고    scopus 로고
    • For a review, see: (a) Walton, J. C.; Studer, A. Acc. Chem. Res. 2005, 38, 794-802. For representative reports:
    • (2005) Acc. Chem. Res. , vol.38 , pp. 794-802
    • Walton, J.C.1    Studer, A.2
  • 33
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    • ref 8f
    • (e) ref 8f.
  • 35
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    • For arguments in favor of a rearomatization step involving a H-abstraction mechanism by AIBN, see: (a) Curran, D. P.; Yu, H.; Liu, H. Tetrahedron 1994, 50, 7343-7366.
    • (1994) Tetrahedron , vol.50 , pp. 7343-7366
    • Curran, D.P.1    Yu, H.2    Liu, H.3
  • 40
    • 0025880852 scopus 로고
    • (f) Bowma, W. R.; Heaney, H.; Jordan, B. M. Tetrahedron 1991, 47, 10119-10128. Oxygen can also be responsible for the aromatization. See:
    • (1991) Tetrahedron , vol.47 , pp. 10119-10128
    • Bowma, W.R.1    Heaney, H.2    Jordan, B.M.3
  • 46
    • 77950235435 scopus 로고    scopus 로고
    • As proposed by one referee, AIBN could also serve as relay for hydrogen delivery, through the intervention of H-AIBN adduct (see ref 13)
    • As proposed by one referee, AIBN could also serve as relay for hydrogen delivery, through the intervention of H-AIBN adduct (see ref 13).
  • 47
    • 0001613451 scopus 로고    scopus 로고
    • As pointed out by one referee, the addition of a methyl radical on a simple alkene is slow and propagation of the radical chain would not be operative (see for these kinetics: Zytowski, T.; Fischer, H. J. Am. Chem. Soc. 1996, 118, 437-439). However, we can anticipate that 8 due to its highly conjugated character is a good acceptor of alkyl radicals.
    • (1996) J. Am. Chem. Soc. , vol.118 , pp. 437-439
    • Zytowski, T.1    Fischer, H.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.