Diels-Alder approach to biaryls (DAB):: Importance of the ortho-nitro moiety in the [4+2] cycloaddition

被引:17
作者
Ashburn, Bradley O. [1 ]
Carter, Rich G. [1 ]
机构
[1] Oregon State Univ, Dept Chem, Corvallis, OR 97331 USA
关键词
D O I
10.1039/b714893c
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A series of nitrophenyl acetylenes were evaluated for their utility in a cycloaddition-cycloreversion approach to poly-substituted biaryls. ortho-Nitrophenyl acetylene consistently provided the target biaryls in superior yields as compared to the meta and para nitro substituted variants.
引用
收藏
页码:255 / 257
页数:3
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共 30 条
[21]   Diels-Alder approach for the construction of halogenated, o-nitro biaryl templates and application to the total synthesis of the Anti-HIV agent siamenol [J].
Naffziger, Michael R. ;
Ashburn, Bradley O. ;
Perkins, Johanna R. ;
Carter, Rich G. .
JOURNAL OF ORGANIC CHEMISTRY, 2007, 72 (26) :9857-9865
[22]   Development of novel steroid sulfatase inhibitors -: I.: Synthesis and biological evaluation of biphenyl-4-O-sulfamates [J].
Okada, M ;
Nakagawa, T ;
Iwashita, S ;
Takegawa, S ;
Fujii, T ;
Koizumi, N .
JOURNAL OF STEROID BIOCHEMISTRY AND MOLECULAR BIOLOGY, 2003, 87 (2-3) :141-148
[23]   DIELS-ALDER REACTIONS OF 2-PYRONES . DIRECTION OF ADDITION REACTION WITH ACETYLENES [J].
REED, JA ;
SCHILLIN.CL ;
TARVIN, RF ;
RETTIG, TA ;
STILLE, JK .
JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (07) :2188-&
[24]   A FACILE ONE-POT SYNTHESIS OF UNSYMMETRICAL BIARYL-2-CARBONITRILES BY NOVEL REACTION OF YLIDENEMALONONITRILES WITH DIENAMINES [J].
SAIN, B ;
SANDHU, JS .
JOURNAL OF ORGANIC CHEMISTRY, 1990, 55 (08) :2545-2546
[25]   REACTIONS OF KETENE ACETALS .14. THE USE OF SIMPLE MIXED VINYLKETENE ACETALS IN THE ANNULATION OF QUINONES [J].
SAVARD, J ;
BRASSARD, P .
TETRAHEDRON, 1984, 40 (18) :3455-3464
[26]  
SMITH SM, 1994, J CHEM SOC P1, P355
[27]   Recent advances in natural product synthesis by using intramolecular Diels-Alder reactions [J].
Takao, K ;
Munakata, R ;
Tadano, K .
CHEMICAL REVIEWS, 2005, 105 (12) :4779-4807
[28]   Big is beautiful -: "Aromaticity" revisited from the viewpoint of macromolecular and supramolecular benzene chemistry [J].
Watson, MD ;
Fechtenkötter, A ;
Müllen, K .
CHEMICAL REVIEWS, 2001, 101 (05) :1267-1300
[29]   TOTAL SYNTHESIS OF THE ANTI-TUMOR ANTIBIOTIC STREPTONIGRIN [J].
WEINREB, SM ;
BASHA, FZ ;
HIBINO, S ;
KHATRI, NA ;
KIM, D ;
PYE, WE ;
WU, TT .
JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 1982, 104 (02) :536-544
[30]   Synthesis and Diels-Alder reactions of 1,2-dimethylene[2.n]metacyclophanes [J].
Yamato, T ;
Miyamoto, S ;
Hironaka, T ;
Miura, Y .
ORGANIC LETTERS, 2005, 7 (01) :3-6