ALD00500
5-Methoxy-1,2,3-triazine
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About This Item
Empirical Formula (Hill Notation):
C4H5N3O
Molecular Weight:
111.10
MDL number:
UNSPSC Code:
12352100
PubChem Substance ID:
NACRES:
NA.22
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
form
powder
storage temp.
2-8°C
Quality Level
Related Categories
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.
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.
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
Regulatory Information
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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 =
Articles
Inverse electron demand Diels-Alder reactions enable total synthesis of natural products with heteroaromatic ring systems.
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