Diverse reactions of 1,4-dilithio-1,3-dienes with nitriles: facile access to tricyclic Delta1-bipyrrolines, multiply substituted pyridines, siloles, and (Z,Z)-dienylsilanes by tuning of substituents on the butadienyl skeleton

Chemistry : a European Journal
Nan YuZhenfeng Xi

Abstract

Addition cyclization of 1,2,3,4-tetrasubstituted 1,4-dilithio-1,3-dienes (Type I) with four equivalents of various aromatic nitriles in the presence of hexamethylphosphoramide (HMPA) gives exclusively fully substituted pyridines in moderate to good yields. Similarly, trisubstituted pyridines can be prepared by the reaction of 2,3-dialkyl- or diaryl-substituted 1,4-dilithio-1,3-dienes (Type II) with nitriles. However, five- or six-membered-ring fused 2,3-disubstituted 1,4-dilithio-1,3-dienes (Type III) reacted with various aromatic and aliphatic nitriles without alpha-hydrogen atoms to afford tricyclic Delta1-bipyrrolines in high yields. The reaction of six-membered-ring fused 2,3-disubstituted 1,4-dilithio-1,3-diene (Type III) with 2-cyanopyridine afforded the corresponding pyridine, and no tricyclic Delta1-bipyrroline was observed. Seven-membered-ring fused dilithiodienes reacted with PhCN or trimethylacetonitrile to afford the corresponding pyridines in good yield. When 1,2,3,4-tetrasubstituted dilithio reagents (Type I) were treated with Me3SiCN, a tandem silylation/intramolecular substitution process readily occurred to yield siloles, whereas the reaction of 2,3-disubstituted dilithio reagents (Types II and III) with Me3SiC...Continue Reading

References

May 29, 2000·Comparative Biochemistry and Physiology. Part A, Molecular & Integrative Physiology·W Miltyk, J A Palka
Dec 12, 2001·Organic Letters·P J CamposM A Rodríguez
Feb 14, 2002·Organic Letters·Morten LysénMikael Begtrup
May 30, 2002·Journal of the American Chemical Society·Jinglong ChenZhenfeng Xi
May 10, 2003·The Journal of Organic Chemistry·Jesper L KristensenMikael Begtrup
Jun 7, 2003·Organic Letters·Moo Je SungJin Kun Cha
Jul 3, 2003·Journal of the American Chemical Society·Ming Yu, Brian L Pagenkopf
Sep 11, 2003·Chemical Reviews·Jesús A Varela, Carlos Saá
May 13, 2004·Chemical Reviews·Sven MangelinckxNorbert De Kimpe
Sep 9, 2004·Chemical Reviews·Peter Langer, Walter Freiberg
Oct 8, 2004·Journal of the American Chemical Society·Satyamaheshwar Peddibhotla, Jetze J Tepe
Feb 24, 2007·Journal of the American Chemical Society·Chao WangZhenfeng Xi

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Citations

Aug 14, 2015·The Journal of Organic Chemistry·Baosheng WeiZhenfeng Xi
Sep 21, 2010·Chemistry, an Asian Journal·Valentine P AnanikovIrina P Beletskaya
Apr 7, 2009·Angewandte Chemie·Bin LiuHaiping Xia
May 11, 2010·Angewandte Chemie·Yoshiaki NakaoTamejiro Hiyama
Jul 27, 2011·Chemical Communications : Chem Comm·Eiji ShirakawaTamio Hayashi
Jul 12, 2012·Journal of the American Chemical Society·Shaoguang ZhangZhenfeng Xi
Nov 15, 2013·Accounts of Chemical Research·Xiao-Yu CaoHaiping Xia
Oct 20, 2010·Accounts of Chemical Research·Zhenfeng Xi
Jan 27, 2018·The Journal of Organic Chemistry·Wubing YaoDeman Han
Nov 7, 2012·Journal of the American Chemical Society·Masahiro OnoeNaoto Chatani

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