Access to a Phthalazine Derivative Through an Angular cis-Quinacridone

Abstract

Intramolecular electrophilic cyclization of a bisanthranilate afforded an angular cis-quinacridone compound, which condensed with hydrazine to give a phthalazine derivative. A [2+2+2] cyclization reaction occurred at the C–N double bond position of phthalazine when reacted with dimethyl acetylenedicarboxylate. The structures of these novel compounds were confirmed by crystallographic analysis. The phthalazine derivative decomposes back to quinacridone at ambient condition in the dark and as a solid with a half lifetime of about 22 months.

Recent advances in versatile pyridazine-cored materials: principles, applications, and challenges

“…There are some difficulties and challenges. For example, the NIR or far IR emission spectra of organic PDs are not easy to achieve even for large p-extended pyrrolopyridazine (pyrroloPD) (PP-1 and PP-2 (Scheme 6)), 122 tetraazaperylenes (TAP-a and TAP-b (Scheme 6)), 55,144 and p-extended phthalazine (2QP (Scheme 6)), 145 diazabenzo[ghi]perylene derivatives (DABP-1, DABP-2 (Scheme 6)). 146 Moreover, the performance of organic thin film optoelectronic devices with PD-based active ingredients remains at relatively low levels, including the charge mobilities (Fig.…”

Recent Advances in Heterocyclic Nanographenes and Other Polycyclic Heteroaromatic Compounds

“… Reagents and conditions: (a) 251 aq. HCl, reflux, 24 h; (b) (1) Na 2 S 2 O 4 , NaOH, H 2 O, 60 °C, 1 h, (2) C n H 2 n +1 Br, Aliquat 336, toluene, 90 °C, 24 h; (c) 252 (1) 2-octylthiophene and n -BuLi (premixed in Et 2 O at −78 °C for 1.5 h), −78 °C, then rt, overnight, (2) SnCl 2 ·H 2 O, rt, 3 h; (d) 253 MsOH, 150 °C, 16 h; (e) (1) NaH, DMF, rt, 2 h, (2) EtI, rt, 24 h; (f) N 2 H 4 ·H 2 O, EtOH, 130 °C, 72 h; (g) toluene, 120 °C, 48 h. …”

“…A selective synthesis of the fused phthalazine derivative 124.8 ( Scheme 124 ) was developed by Zhu and Zhang. 253 Upon heating the known diester 124.5 in methanesulfonic acid, the 2-fold Friedel–Crafts acylation took place regioselectively to give the angularly fused product 124.6 rather than the isomeric, linearly fused quinacridone skeleton. Compound 124.6 was ethylated at both NH groups and condensed with hydrazine to yield the tetraazapyrenoid 124.8 in 36% over two steps.…”

Azaacenes Based Electroactive Materials: Preparation, Structure, Electrochemistry, Spectroscopy and Applications—A Critical Review

“…It should be noted that azaacenes of very diversified nitrogen atoms distribution can be obtained via condensation of amines with ketones. For example, Zhu et al [ 48 ] prepared phthalazine derivatives in which nitrogen atoms occupied adjacent positions.…”