2-Dimethoxymethyl[1,8]naphthyridine
[CAS# 204452-90-4]

Identification

• Classification: Organic raw materials >> Aryl compounds >> Naphthalenes
• Name: 2-Dimethoxymethyl[1,8]naphthyridine
• Molecular Formula: C₁₁H₁₂N₂O₂
• Molecular Weight: 204.23
• CAS Registry Number: 204452-90-4
• SMILES: COC(C1=NC2=C(C=CC=N2)C=C1)OC

Properties

• Solubility: Sparingly soluble (17 g/L) (25 °C), Calc.^*
• Density: 1.181±0.06 g/cm³ (20 °C 760 Torr), Calc.^*
• Melting point: 53.5-55.5 °C^**
• Boiling point: 283.0±35.0 °C (760 Torr), Calc.^*
• Flash point: 103.8±16.2 °C, Calc.^*
• Index of refraction: 1.586 (Calc.)^*

^* Calculated using Advanced Chemistry Development (ACD/Labs) Software V11.02 (©1994-2013 ACD/Labs)

^** Yasuda, Nobuyoshi

Safety Data

• Hazard Symbols: GHS07 Warning
• Risk Statements: H302
• Safety Statements: P264-P270-P301+P317-P330-P501

Discovery and Applications

2-Dimethoxymethyl[1,8]naphthyridine is a specialized chemical compound belonging to the naphthyridine family, characterized by a bicyclic structure containing two nitrogen atoms within a fused aromatic system. In this molecule, a dimethoxymethyl group is attached at the 2-position of the [1,8]naphthyridine core, offering unique chemical properties that have been exploited in various fields, particularly in pharmaceutical research and organic synthesis.

The discovery of 2-dimethoxymethyl[1,8]naphthyridine can be traced to investigations into substituted naphthyridines, a class of compounds well-known for their broad range of biological activities. Researchers sought to develop derivatives that would allow for further functionalization or that could serve as intermediates in the preparation of biologically active molecules. The introduction of a dimethoxymethyl group provides a stable, electron-rich substituent that can be selectively modified under specific reaction conditions, enhancing the utility of the parent structure.

Applications of 2-dimethoxymethyl[1,8]naphthyridine are mainly focused on its role as a synthetic intermediate. The dimethoxymethyl group can act as a protected form of an aldehyde, which upon deprotection under acidic conditions, releases the corresponding aldehyde functionality. This conversion is highly valuable in multi-step synthetic routes where aldehyde groups are reactive and need to be introduced at a later stage without affecting earlier transformations. Therefore, 2-dimethoxymethyl[1,8]naphthyridine has been used in the synthesis of more complex naphthyridine derivatives that possess significant biological activities.

In medicinal chemistry, naphthyridine derivatives have attracted attention due to their antimicrobial, antiviral, anticancer, and anti-inflammatory properties. The [1,8]naphthyridine scaffold, in particular, resembles natural nucleic acid bases and has been studied for its potential to interact with biological macromolecules such as DNA and RNA. Although 2-dimethoxymethyl[1,8]naphthyridine itself has not been widely reported as a final drug candidate, it has served as a precursor in the development of compounds designed to inhibit key enzymes or bind to nucleic acid structures with high specificity.

Organic chemists have utilized 2-dimethoxymethyl[1,8]naphthyridine to construct libraries of heterocyclic compounds through reactions such as condensation, cyclization, and cross-coupling. The presence of the electron-rich dimethoxymethyl group can influence the reactivity of the naphthyridine ring, allowing for selective transformations that would be difficult to achieve with unsubstituted naphthyridines. In some synthetic schemes, the compound has enabled regioselective functionalization, facilitating the exploration of structure-activity relationships in pharmacological studies.

Moreover, the development of methods to introduce and subsequently remove the dimethoxymethyl group in a controlled manner has added to the synthetic versatility of the [1,8]naphthyridine core. Mild acidic hydrolysis can efficiently cleave the dimethoxymethyl moiety to yield the corresponding aldehyde, opening the way for subsequent reactions such as reductive amination, aldol condensation, or Wittig olefination. These transformations have been critical in assembling complex molecular frameworks relevant to drug discovery and development.

Overall, 2-dimethoxymethyl[1,8]naphthyridine represents a strategically important building block in synthetic organic chemistry. Its discovery has expanded the toolkit available for the construction of diverse naphthyridine-based compounds, which continue to play a significant role in the search for new therapeutic agents and in the study of biologically relevant chemical space.