Literature DB >> 21488676

Scope of the inverse electron demand Diels-Alder reactions of 1,2,3-triazine.

Erin D Anderson1, Dale L Boger.   

Abstract

An examination of the scope of the inverse electron demand Diels-Alder reactions of the parent unsubstituted 1,2,3-triazine is described including the first report of its unique capabilities for participating in previously unexplored [4 + 2] cycloaddition reactions with heterodienophiles.

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Year:  2011        PMID： 21488676      PMCID： PMC3093666          DOI： 10.1021/ol2007428

Source DB:  PubMed          Journal:  Org Lett        ISSN： 1523-7052            Impact factor:   6.005


  24 in total

1.  Total synthesis of anhydrolycorinone utilizing sequential intramolecular Diels-Alder reactions of a 1,3,4-oxadiazole.

Authors:  Scott E Wolkenberg; Dale L Boger
Journal:  J Org Chem       Date:  2002-10-18       Impact factor: 4.354

2.  Intramolecular Diels-Alder and tandem intramolecular Diels-Alder/1,3-dipolar cycloaddition reactions of 1,3,4-oxadiazoles.

Authors:  Gordon D Wilkie; Gregory I Elliott; Brian S J Blagg; Scott E Wolkenberg; Danielle R Soenen; Michael M Miller; Scott Pollack; Dale L Boger
Journal:  J Am Chem Soc       Date:  2002-09-25       Impact factor: 15.419

3.  Total synthesis of piericidin A1 and B1.

Authors:  Martin J Schnermann; Dale L Boger
Journal:  J Am Chem Soc       Date:  2005-11-16       Impact factor: 15.419

4.  Asymmetric total synthesis of vindoline.

Authors:  Daisuke Kato; Yoshikazu Sasaki; Dale L Boger
Journal:  J Am Chem Soc       Date:  2010-03-24       Impact factor: 15.419

5.  Total synthesis of ningalin B utilizing a heterocyclic azadiene Diels-Alder reaction and discovery of a new class of potent multidrug resistant (MDR) reversal agents.

Authors:  D L Boger; D R Soenen; C W Boyce; M P Hedrick; Q Jin
Journal:  J Org Chem       Date:  2000-04-21       Impact factor: 4.354

6.  Two novel 1,2,4,5-tetrazines that participate in inverse electron demand Diels-Alder reactions with an unexpected regioselectivity.

Authors:  Akiyuki Hamasaki; Richard Ducray; Dale L Boger
Journal:  J Org Chem       Date:  2006-01-06       Impact factor: 4.354

7.  Total synthesis of natural (+)- [corrected] and ent-(-)-4-desacetoxy-6,7-dihydrovindorosine [corrected] and natural and ent-minovine: oxadiazole tandem intramolecular Diels-Alder/1,3-dipolar cycloaddition reaction.

Authors:  Zhong Qing Yuan; Hayato Ishikawa; Dale L Boger
Journal:  Org Lett       Date:  2005-02-17       Impact factor: 6.005

8.  Synthesis and inverse electron demand Diels-Alder reactions of 3,6-bis(3,4-dimethoxybenzoyl)-1,2,4,5-tetrazine.

Authors:  Danielle R Soenen; Jeffrey M Zimpleman; Dale L Boger
Journal:  J Org Chem       Date:  2003-05-02       Impact factor: 4.354

9.  Total synthesis of vinblastine, vincristine, related natural products, and key structural analogues.

Authors:  Hayato Ishikawa; David A Colby; Shigeki Seto; Porino Va; Annie Tam; Hiroyuki Kakei; Thomas J Rayl; Inkyu Hwang; Dale L Boger
Journal:  J Am Chem Soc       Date:  2009-04-08       Impact factor: 15.419

10.  Diastereoselective Diels-Alder reactions of N-sulfonyl-1-aza-1,3-butadienes with optically active enol ethers: an asymmetric variant of the 1-azadiene Diels-Alder reaction.

Authors:  Ryan C Clark; Steven S Pfeiffer; Dale L Boger
Journal:  J Am Chem Soc       Date:  2006-03-01       Impact factor: 15.419
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  15 in total

1.  Total synthesis of dihydrolysergic acid and dihydrolysergol: development of a divergent synthetic strategy applicable to rapid assembly of D-ring analogs.

Authors:  Kiyoun Lee; Yam B Poudel; Christopher M Glinkerman; Dale L Boger
Journal:  Tetrahedron       Date:  2015-09-02       Impact factor: 2.457

2.  Synthesis, Characterization, and Rapid Cycloadditions of 5-Nitro-1,2,3-triazine.

Authors:  Christopher M Glinkerman; Dale L Boger
Journal:  Org Lett       Date:  2018-04-16       Impact factor: 6.005

3.  Cycloadditions of 1,2,3-Triazines Bearing C5-Electron Donating Substituents: Robust Pyrimidine Synthesis.

Authors:  Christopher M Glinkerman; Dale L Boger
Journal:  Org Lett       Date:  2015-07-14       Impact factor: 6.005

4.  Inverse electron demand Diels-Alder reactions of 1,2,3-triazines: pronounced substituent effects on reactivity and cycloaddition scope.

Authors:  Erin D Anderson; Dale L Boger
Journal:  J Am Chem Soc       Date:  2011-07-19       Impact factor: 15.419

5.  Domino Reaction Sequence for the Synthesis of [2.2.2]Diazabicycloalkenes and Base-Promoted Cycloreversion to 2-Pyridone Alkaloids.

Authors:  Nicholas H Angello; Robert E Wiley; Tristan G Elmore; Ryan S Perry; Jonathan R Scheerer
Journal:  Org Lett       Date:  2018-08-10       Impact factor: 6.005

6.  Direct Synthesis of β-Aminoenals through Reaction of 1,2,3-Triazine with Secondary Amines.

Authors:  Ryan E Quiñones; Christopher M Glinkerman; Kaicheng Zhu; Dale L Boger
Journal:  Org Lett       Date:  2017-06-28       Impact factor: 6.005

Review 7.  Inverse Electron Demand Diels-Alder Reactions of Heterocyclic Azadienes, 1-Aza-1,3-Butadienes, Cyclopropenone Ketals, and Related Systems. A Retrospective.

Authors:  Jiajun Zhang; Vyom Shukla; Dale L Boger
Journal:  J Org Chem       Date:  2019-05-23       Impact factor: 4.354

8.  Reaction Scope of Methyl 1,2,3-Triazine-5-carboxylate with Amidines and the Impact of C4/C6 Substitution.

Authors:  Ryan E Quiñones; Zhi-Chen Wu; Dale L Boger
Journal:  J Org Chem       Date:  2021-09-09       Impact factor: 4.198

9.  Catalysis of Heterocyclic Azadiene Cycloaddition Reactions by Solvent Hydrogen Bonding: Concise Total Synthesis of Methoxatin.

Authors:  Christopher M Glinkerman; Dale L Boger
Journal:  J Am Chem Soc       Date:  2016-09-14       Impact factor: 15.419

10.  Direct palladium(II)-catalyzed synthesis of arylamidines from aryltrifluoroborates.

Authors:  Jonas Sävmarker; Jonas Rydfjord; Johan Gising; Luke R Odell; Mats Larhed
Journal:  Org Lett       Date:  2012-04-17       Impact factor: 6.005
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