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ALD00500

Sigma-Aldrich

5-Methoxy-1,2,3-triazine

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About This Item

Empirický vzorec (Hillův zápis):
C4H5N3O
Molekulová hmotnost:
111.10
UNSPSC Code:
12352100
PubChem Substance ID:
329772693
NACRES:
NA.22

form

powder

Quality Level

100

storage temp.

2-8°C

SMILES string

COC1=CN=NN=C1

InChI

1S/C4H5N3O/c1-8-4-2-5-7-6-3-4/h2-3H,1H3

InChI key

HVBZCUMRMKODNE-UHFFFAOYSA-N

General description

5-Methoxy-1,2,3-triazine is a 1,2,3-triazine derivative bearing electron-donating substituent. It participates in the inverse electron demand Diels-Alder reactions. 5-Methoxy-1,2,3-triazine readily reacts with amidines. It can be prepared from 4-methoxypyrazole.

Application

1, 2, 3-Triazines have shown to be reactive substrates in inverse electron demand Diels-Alder strategies. Recent examples by Boger and coworkers utilize this reactive motif in the construction of highly functionalized N-containing heterocycles.
5-Methoxy-1,2,3-triazine may be used in the synthesis of nitrogen-containing heterocyclic compounds.

Legal Information

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

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Osvědčení o analýze (COA)

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Christopher M Glinkerman et al.
Organic letters, 17(16), 4002-4005 (2015-07-15)
The examination of the cycloaddition reactions of 1,2,3-triazines 17-19, bearing electron-donating substituents at C5, are described. Despite the noncomplementary 1,2,3-triazine C5 substituents, amidines were found to undergo a powerful cycloaddition to provide 2,5-disubstituted pyrimidines in excellent yields (42-99%; EDG =

Sortimentní položky

Inverse Electron Demand Diels-Alder Reactions

Inverse electron demand Diels-Alder reactions enable total synthesis of natural products with heteroaromatic ring systems.

Související obsah

Boger Group – Professor Product Portal

As the exploration of the properties of complex natural products becomes increasingly more sophisticated with the technological advances being made in their screening and evaluation and as structural details of their interaction with biological targets becomes more accessible, the importance and opportunities for providing unique solutions to complex biological problems has grown. The Boger Lab addresses these challenging problems by understanding the complex solutions and subtle design elements that nature has provided in the form of a natural product and work to extend the solution through rational design elements to provide more selective, more efficacious, or more potent agents designed specifically for the problem or target under investigation. The resulting efforts have reduced many difficult or intractable synthetic challenges to manageable problems providing an approach not only to the natural product but one capable of simple extrapolation to a series of structural analogs with improved selectivity and efficacy.

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