64482-94-6

Usage

Structure

Bicyclic heterocycle with a six-membered ring fused to a five-membered ring

Functional groups

a. Two methyl groups on the six-membered ring
b. Two methyl groups on the five-membered ring
c. One nitrogen atom in the five-membered ring

Applications

a. Precursor in the synthesis of pharmaceuticals and agrochemicals
b. Potential therapeutic agent due to biological activity
c. Building block in organic synthesis for functionalized derivatives

Reactivity

Can undergo various chemical reactions to produce functionalized derivatives

Importance

Significant applications in pharmaceutical and chemical industries

Upstream product

• 20734-56-9 1,8-dimethylaminonaphthalene 
• 67-64-1 acetone 
• 6364-17-6 2,3-dihydro-2,2-dimethylperimidine 
• 74-88-4 methyl iodide 

Downstream Products

• 20734-58-1 N,N,N',N'-tetramethyl-1,8-diaminonaphthalene 
• 20734-56-9 1,8-dimethylaminonaphthalene 

Relevant academic research and scientific papers

Poly(1,1-bis(dialkylamino)propan-1,3-diyl)s; Conformationally-controlled oligomers bearing electroactive groups

The design of polymers with repeating [C(NR2)2CH 2CH2] units which may simultaneously provide conformational control and contain repeating electroactive centres is discussed; (NR2)2 groups would be ideally provided by ortho-phenylenediamine derivatives, with 1,8-diaminonaphthalenes as alternatives. Oligomers containing 1,8-bis(methylamino)naphthalenes, up to the hexamer, were obtained by condensation of oligomers of CH3[COCH 2CH2]nCOCH3 with 1,8-bis(methylamino)naphthalene, but attempts to prepare related oligomers from 1,2-bis(alkylamino)benzenes were unsuccessful, as only terminal ketone groups could be converted to aminals. Evidence for a strong preference for all-anti conformations of the main chain in the naphthalenediamine oligomers is provided by ring current effects on 1H NMR shifts, and by X-ray structures, which also provide evidence of intercalation in the solid state. Electrochemical studies of these oligomers show irreversible oxidation of oligomers in solution, but oxidation of longer oligomers leads to the deposition of a reddish-pink insoluble material which shows two reversible oxidation waves. Possible interpretation of these results is discussed. The Royal Society of Chemistry 2009.

peri-Naphthylenediamines 31.* Study of interconversions of 2,3-dihydroperimidines and 1,8-bis(dialkylamino)naphthaienes. Convenient synthesis of 1,2,2,3-tetramethyl-2,3-dihydroperimidine and a monoisopropyl analog of the "proton sponge"

Efficient procedures were developed for the two-step synthesis of 1,2,2,3-tetramethyl-2,3-dihydroperimidines and for the one-step synthesis of 1,3-dimethyl-2,3-dihydroperimidines starting from 1,8-diaminonaphthalenes. New possibilities of the use of 2,3-dihydroperimidinium salts in the synthesis of 1,8-bis(dialkylamino)naphthalenes ("proton sponges") containing the N-isopropyl group along with the N-methyl groups were demonstrated. The 1,1,2,2,3-pentamethyl-2,3-dihydroperimidinium cation exists in the acyclic iminium form responsible for its high reactivity.

Process for preparing 2,3-dihydro-1,3-dialkyl-2,3-dialkyl perimidines and N,N-'-dialkyl-1,8-naphthalene diamines

Processes for preparing 2,3-dihydro-1,3-dialkyl-2,2-dialkyl perimidines and N,N'-dialkyl-1,8-naphthalene diamines are disclosed. The 2,3-dihydro-1,3-dialkyl-2,2-dialkyl perimidines are prepared by alkylating 2,3-dihydro-2,2-dialkyl perimidines with an alkylating agent in a water miscible organic solvent at room temperature to 80° C. in the presence of water and an inorganic base. N,N'-dialkyl-1,8-naphthalene diamines are prepared by hydrolyzing the 2,3-dihydro-1,3-dialkyl-2,2-dialkyl perimidines with strong aqueous acid in an aqueous organic solvent and removing a ketone by-product and the aqueous organic solvent by codistillation.

Synthesis and Characterization of Tetra(azo)2,3-Dihydroperimidine Dyes for Guest-Host Liquid Crystals

The synthesis and characterization of several tetra(azo)-2,3-dihydroperimidine dyes with alkyl substituents in the 1,2, and 3 positions are described.The dyes have intense blue colors, high order parameters and high solubilities in liquid crystal host solvents.Order parameters are enhanced with longer alkyl substituents at the 2-position.Two of the dyes exhibit thermal transitions consistent with formation of liquid crystal phases.

Electronic Structure of Heterospirenes-PE Spectroscopic Investigations

The synthesis of the heterospirenes 1-9 is described and their He I photoelectron (PE) spectra are recorded.The assignment of the first PE bands is based on a comparison with fragment molecules and on molecular orbital calculations using semiempirical methods (PPP, MINDO/3). in the case of 1, 2, 4, and 5 strong spirointeraction has been elucidated.For 3 the analysis of the spectrum is hampered due to the strong overlap of the bands while for 6 the nonplanarity brings about a reduction of spirointeractions.For 7-9 the interaction between both fragments could not be detected.