Literature DB >> 21548654

Superacid-promoted additions involving vinyl-substituted pyrimidines, quinoxalines, and quinazolines: mechanisms correlated to charge distributions.

Yiliang Zhang1, Matthew R Sheets, Erum K Raja, Kenneth N Boblak, Douglas A Klumpp.   

Abstract

The superacid-promoted reactions of vinyl-substituted N-heterocycles have been studied. Diprotonated pyrimidines, quinoxalines, and quinazolines exhibit an unusual regioelectronic effect that controls the type of addition reaction observed. Depending on the ring position of the vinyl substituent, either conjugate addition or Markovnikov addition occurs. The mode of addition has been shown to correlate well to NBO calculated charges.

Entities:  

Mesh：

Substances：

Year:  2011        PMID： 21548654      PMCID： PMC3169346          DOI： 10.1021/ja202557z

Source DB:  PubMed          Journal:  J Am Chem Soc        ISSN： 0002-7863            Impact factor:   15.419


  6 in total

1.  Bis annelations via 6-methyl-2-vinylpyridine. An efficient synthesis of dl-D-homoestrone.

Authors:  S Danishefsky; P Cain; A Nagel
Journal:  J Am Chem Soc       Date:  1975-01-22       Impact factor: 15.419

2.  Pd/P(t-Bu)(3): a mild and general catalyst for Stille reactions of aryl chlorides and aryl bromides.

Authors:  Adam F Littke; Lothar Schwarz; Gregory C Fu
Journal:  J Am Chem Soc       Date:  2002-06-05       Impact factor: 15.419

3.  Tuned methods for conjugate addition to a vinyl oxadiazole; synthesis of pharmaceutically important motifs.

Authors:  Alan R Burns; Jennifer H Kerr; William J Kerr; Joanna Passmore; Laura C Paterson; Allan J B Watson
Journal:  Org Biomol Chem       Date:  2010-04-28       Impact factor: 3.876

4.  Superacid-catalyzed reactions of olefinic pyrazines: an example of anti-Markovnikov addition involving superelectrophiles.

Authors:  Yiliang Zhang; Jason Briski; Yun Zhang; Rendy Rendy; Douglas A Klumpp
Journal:  Org Lett       Date:  2005-06-09       Impact factor: 6.005

5.  Dicationic electrophiles from olefinic amines in superacid.

Authors:  Yun Zhang; Aaron McElrea; Gregorio V Sanchez; Dat Do; Alma Gomez; Sharon L Aguirre; Rendy Rendy; Douglas A Klumpp
Journal:  J Org Chem       Date:  2003-06-27       Impact factor: 4.354

6.  Conjugate addition of nucleophiles to the vinyl function of 2-chloro-4-vinylpyrimidine derivatives.

Authors:  Elizabeth Raux; Jeffrey Klenc; Ava Blake; Jarosław Saczewski; Lucjan Strekowski
Journal:  Molecules       Date:  2010-03-19       Impact factor: 4.411
  6 in total
  4 in total

1.  Charge delocalization and enhanced acidity in tricationic superelectrophiles.

Authors:  Rajasekhar Reddy Naredla; Chong Zheng; Sten O Nilsson Lill; Douglas A Klumpp
Journal:  J Am Chem Soc       Date:  2011-07-27       Impact factor: 15.419

Review 2.  Superelectrophiles: Recent Advances.

Authors:  Douglas A Klumpp; Maksim V Anokhin
Journal:  Molecules       Date:  2020-07-19       Impact factor: 4.411

3.  Efficient Tandem Addition/Cyclization for Access to 2,4-Diarylquinazolines via Catalytic Carbopalladation of Nitriles.

Authors:  Julin Gong; Kun Hu; Yetong Zhang; Yinlin Shao; Tianxing Cheng; Maolin Hu; Jiuxi Chen
Journal:  Molecules       Date:  2019-01-28       Impact factor: 4.411

4.  Hydrogen Transfer-Mediated Multicomponent Reaction for Direct Synthesis of Quinazolines by a Naphthyridine-Based Iridium Catalyst.

Authors:  Zhenda Tan; Zhongxin Fu; Jian Yang; Yang Wu; Liang Cao; Huanfeng Jiang; Juan Li; Min Zhang
Journal:  iScience       Date:  2020-03-21
  4 in total

北京卡尤迪生物科技股份有限公司 © 2022-2023.