A Base-Mediated 6-exo-trig versus 6-exo-dig Carbocyclization Strategy for the Synthesis of Functionalized Biaryl Compounds

被引：6

作者：

Yadav, Pratik ^{[1
]}

Shaw, Ranjay ^{[1
]}

Panwar, Rahul ^{[1
]}

Sahu, Satya Narayan ^{[1
]}

Kumar, Abhinav ^{[2
]}

Pratap, Ramendra ^{[1
]}

机构：

[1] Univ Delhi, Dept Chem, North Campus, Delhi 110007, India

[2] Univ Lucknow, Dept Chem, Lucknow 226009, Uttar Pradesh, India

来源：

ASIAN JOURNAL OF ORGANIC CHEMISTRY | 2017年 / 6卷 / 10期

关键词：

Baldwin's rules; cyclization; cabocycles; chemoselectivity; ring transformation; ORGANIC-SYNTHESIS; CHEMICAL SPACE; RING-CLOSURE; PHENANTHRENES; CYCLOISOMERIZATION; 2H-PYRAN-2-ONES; VERSATILITY; DERIVATIVES; CHROMENES; ALKYNES;

D O I：

10.1002/ajoc.201700319

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A base-mediated carbocyclization study has been performed between two allowed Baldwin cyclization modes (6-exo-trig and 6-exo-dig) and it was found that 6-exo-trig cyclization was preferred over 6-exo-dig. Allyl cyanide was found to be suitable and efficient pronucleophile for this investigation and two sp(2)-sp(2) transition-metal-free C-C bond formations took place in a single operation to yield two differently functionalized biaryl compounds.

引用

页码：1394 / 1397

页数：4

共 32 条

[1]

Abu SohelS.M., 2009, Chem. Soc. Rev, V38, P2269

[2] A diversity oriented synthesis of highly functionalized unsymmetrical biaryls through carbanion induced ring transformation of 2H-pyran-2-ones [J].

Agarwal, N ;

Saxena, AS ;

Farhanullah ;

Goel, A ;

Ram, VJ .

TETRAHEDRON, 2002, 58 (43) :8793-8798

[3]

[Anonymous], 2001, ANGEW CHEM, V113, P2156

[4] Transition-Metal-Free Synthesis of Benzimidazoles Mediated by KOH/DMSO [J].

Baars, Hannah ;

Beyer, Astrid ;

Kohlhepp, Stefanie V. ;

Bolm, Carsten .

ORGANIC LETTERS, 2014, 16 (02) :536-539

[5] RULES FOR RING-CLOSURE [J].

BALDWIN, JE .

JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1976, (18) :734-736

[6] Bioactivity-Guided Navigation of Chemical Space [J].

Bon, Robin S. ;

Waldmann, Herbert .

ACCOUNTS OF CHEMICAL RESEARCH, 2010, 43 (08) :1103-1114

[7]

CCDC, 15205633C CCDC

[8]

Farhanullah, 2003, J ORG CHEM, V68

[9] Copper-catalyzed 1,2-double amination of 1-halo-1-alkynes. Concise synthesis of protected tetrahydropyrazines and related heterocyclic compounds [J].

Fukudome, Yasuhiro ;

Naito, Hiroyuki ;

Hata, Takeshi ;

Urabe, Hirokazu .

JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2008, 130 (06) :1820-+

[10] Cyclizations of Alkynes: Revisiting Baldwin's Rules for Ring Closure [J].

Gilmore, Kerry ;

Alabugin, Igor V. .

CHEMICAL REVIEWS, 2011, 111 (11) :6513-6556

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