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Intermolecular Double Prins-Type Cyclization: A Facile and Efficient Synthesis of 1,6-Dioxecanes
Ullapu, Punna Reddy,Min, Sun-Joon,Chavre, Satish N.,Choo, Hyunah,Lee, Jae Kyun,Pae, Ae Nim,Kim, Youseung,Chang, Moon Ho,Cho, Yong Seo WILEY-VCH Verlag 2009 Angewandte Chemie Vol.48 No.12
<P>Double or nothing: The title reaction converts a range of aromatic aldehydes and allenylmethyl/allyl silanes into 1,6-dioxecane derivatives in good to excellent yields (see scheme; Ar=aryl, Tf=triflate, THF=tetrahydrofuran, TMS=trimethylsilyl). In addition, the bisdiene product has been transformed into the corresponding tricyclic compound through a Diels–Alder reaction. <img src='wiley_img/14337851-2009-48-12-ANIE200804576-content.gif' alt='wiley_img/14337851-2009-48-12-ANIE200804576-content'> </P> <B>Graphic Abstract</B> <P>Double or nothing: The title reaction converts a range of aromatic aldehydes and allenylmethyl/allyl silanes into 1,6-dioxecane derivatives in good to excellent yields (see scheme; Ar=aryl, Tf=triflate, THF=tetrahydrofuran, TMS=trimethylsilyl). In addition, the bisdiene product has been transformed into the corresponding tricyclic compound through a Diels–Alder reaction. <img src='wiley_img/14337851-2009-48-12-ANIE200804576-content.gif' alt='wiley_img/14337851-2009-48-12-ANIE200804576-content'> </P>
Ullapu, Punna Reddy,Ku, Su-Jin,Choi, Yeon-Hee,Park, Ji-Yeon,Han, So-Yeop,Baek, Du-Jong,Lee, Jae-Kyun,Pae, Ae-Nim,Min, Sun-Joon,Cho, Yong-Seo Korean Chemical Society 2011 Bulletin of the Korean Chemical Society Vol.32 No.suppl8
The synthesis and biological evaluation of 1-heteroarylmethyl 1,4-diazepane derivatives as potential T-type calcium channel blockers is described. In this study, we have identified the compound 21i exhibiting the most potent T-type calcium channel blocking activity with $IC_{50}$ value of 0.20 ${\mu}M$, which is superior to that of mibefradil.
Punna Reddy Ullapu,구수진,최연희,박지연,한소엽,백두종,이재균,배애님,민선준,조용서 대한화학회 2011 Bulletin of the Korean Chemical Society Vol.32 No.8
The synthesis and biological evaluation of 1-heteroarylmethyl 1,4-diazepane derivatives as potential T-type calcium channel blockers is described. In this study, we have identified the compound 21i exhibiting the most potent T-type calcium channel blocking activity with IC_50 value of 0.20 μM, which is superior to that of mibefradil.
TMSOTf-Promoted Addition of Alkynes to Aldehydes: A Novel Synthesis of Chroman-4-ones
Park, Ji Yeon,Ullapu, Punna Reddy,Choo, Hyunah,Lee, Jae Kyun,Min, Sun-Joon,Pae, Ae Nim,Kim, Youseung,Baek, Du-Jong,Cho, Yong Seo WILEY-VCH Verlag 2008 EUROPEAN JOURNAL OF ORGANIC CHEMISTRY Vol.2008 No.32
<P>A novel synthetic method to prepare chalcones 2 and chroman-4-ones 3 by TMSOTf-promoted addition of alkynes 1 to various aldehydes has been developed. The ratios of chalcones 2, chroman-4-ones 3 and hydrated products 4 varied depending upon the substituents R (nBu, phenyl, H and TMS) on the alkynes 1. We also describe the transformation of the chalcones 2 to the corresponding chroman-4-ones 3 under basic conditions. (© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2008)</P> <B>Graphic Abstract</B> <P>A novel synthetic method to prepare chalcones and chroman-4-ones by TMSOTf-promoted addition of alkynes to various aldehydes has been developed. The ratios of chalcones, chroman-4-ones and hydratedproducts vary depending upon the substituents on the alkynes. We also describe the transformation of the chalcones to the corresponding chroman-4-ones under basic conditions. <img src='wiley_img/1434193X-2008-2008-32-EJOC200800782-fig000.gif' alt='wiley_img/1434193X-2008-2008-32-EJOC200800782-fig000'> </P>