Literature DB >> 29659291

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

Christopher M Glinkerman1, Dale L Boger1.   

Abstract

The synthesis, characterization, and a study of the cycloaddition reactions of 5-nitro-1,2,3-triazine (3) are reported. The electron-deficient nature of 3 permits rapid cycloaddition with a variety of electron-rich dienophiles, including amidines, enamines, enol ethers, ynamines, and ketene acetals in high to moderate yields. 1H NMR studies of a representative cycloaddition reaction between 3 and an amidine revealed a remarkable reaction rate and efficiency (1 mM, <60 s, CD3CN, 23 °C, >95%).

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Year:  2018        PMID： 29659291      PMCID： PMC5935562          DOI： 10.1021/acs.orglett.8b00825

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


  25 in total

1.  CC-1065 and the Duocarmycins: Synthetic Studies.

Authors:  Dale L. Boger; Christopher W. Boyce; Robert M. Garbaccio; Joel A. Goldberg
Journal:  Chem Rev       Date:  1997-05-08       Impact factor: 60.622

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 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

4.  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

Review 5.  Click chemistry in complex mixtures: bioorthogonal bioconjugation.

Authors:  Craig S McKay; M G Finn
Journal:  Chem Biol       Date:  2014-09-18

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

7.  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

8.  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

9.  Tetrazine-based cycloadditions: application to pretargeted live cell imaging.

Authors:  Neal K Devaraj; Ralph Weissleder; Scott A Hilderbrand
Journal:  Bioconjug Chem       Date:  2008-12       Impact factor: 4.774

Review 10.  Total synthesis of vinblastine, related natural products, and key analogues and development of inspired methodology suitable for the systematic study of their structure-function properties.

Authors:  Justin E Sears; Dale L Boger
Journal:  Acc Chem Res       Date:  2015-01-14       Impact factor: 22.384
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  3 in total

Review 1.  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

2.  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

3.  Mechanistic Insights into the Reaction of Amidines with 1,2,3-Triazines and 1,2,3,5-Tetrazines.

Authors:  Zhi-Chen Wu; K N Houk; Dale L Boger; Dennis Svatunek
Journal:  J Am Chem Soc       Date:  2022-06-06       Impact factor: 16.383
  3 in total

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