A new synthetic route to substituted tetracenes and pentacenes via stereoselective [4+2] cycloadditions of 1,4-dihydro-1,4-epoxynaphthalene and isobenzofuran

Chemical Communications : Chem Comm
Shohei EdaToshiyuki Hamura

Abstract

Stereoselective [4+2] cycloadditions of 1,4-dihydro-1,4-epoxynaphthalene and isobenzofuran were described. Among several possibilities, syn-exo and/or anti-endo isomers were selectively produced depending on the substitution pattern of the reactants. Importantly, the syn-exo isomer underwent acid promoted aromatization, affording the corresponding tetracene. These findings enabled us to prepare a substituted pentacene with electron withdrawing groups.

References

Sep 20, 2001·Journal of the American Chemical Society·J E AnthonyS R Parkin
May 7, 2004·Organic Letters·Marcia M PayneJohn E Anthony
Oct 9, 2004·The Journal of Organic Chemistry·Nicolas PichonJacques Maddaluno
Jul 16, 2005·Organic Letters·Christopher R SwartzGeorge G Malliaras
Jan 26, 2006·Journal of the American Chemical Society·Qian MiaoColin Nuckolls
Sep 21, 2006·Journal of the American Chemical Society·Yoichiro KuninobuKazuhiko Takai
Dec 15, 2006·Chemical Reviews·John E Anthony
Jul 28, 2007·The Journal of Organic Chemistry·Sujeewa S PalayangodaDouglas C Neckers
Nov 30, 2007·Angewandte Chemie·John E Anthony
Jun 20, 2008·Organic Letters·Scott T MeekTimothy M Swager
Sep 4, 2008·Organic Letters·Dan LehnherrRik R Tykwinski
Nov 14, 2008·Journal of the American Chemical Society·Irvinder KaurGlen P Miller
Feb 27, 2009·Journal of the American Chemical Society·Ming Lee TangZhenan Bao
Sep 4, 2009·The Journal of Organic Chemistry·Melissa BallantineWilliam Tam
Oct 23, 2009·Chemistry : a European Journal·Dan LehnherrRik R Tykwinski
Feb 19, 2010·Chemical Reviews·Kathrin Prantz, Johann Mulzer
Sep 29, 2011·The Journal of Organic Chemistry·Jennifer TsoungMark Lautens
Nov 13, 2012·Chemical Communications : Chem Comm·Ming ChenYuanhong Liu
Dec 12, 2012·Organic & Biomolecular Chemistry·Jun HuAlbert S C Chan

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Citations

Oct 30, 2015·Molecules : a Journal of Synthetic Chemistry and Natural Product Chemistry·Shohei Eda, Toshiyuki Hamura
Mar 11, 2016·ACS Nano·Justus KrügerDiego Peña
Feb 3, 2018·Chemical Communications : Chem Comm·Kseniya K BorisovaFedor I Zubkov
Aug 3, 2018·Chemistry : a European Journal·Kei KitamuraToshiyuki Hamura
Oct 18, 2018·Chemistry : a European Journal·Suguru MatsuokaToshiyuki Hamura
Nov 22, 2018·Organic & Biomolecular Chemistry·Kei KitamuraToshiyuki Hamura
Nov 13, 2020·Chemical Communications : Chem Comm·Kei KitamuraToshiyuki Hamura

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