Synthesis and electrochemical properties of benzo[b]naphtho[2,3-e][1,4]-dioxin-6,11-quinones and their N,N'-dicyano quinone diimine derivatives

Abstract

evaporated in vacuo. The residue was purified by radial chromatography, eluting with 10% MeOH/CH2Cl2 to yield 46 mg (44%) of product: [a]p -125°(c 0.2, CHC13) (lit. -128).23Reduction of Egenine and Corytensine. To a solution of the phthalide isoquinoline hemiacetal in ethanol was added 1 molar equiv of NaBH4. The reaction mixture was stirred overnight at room temperature. After removal of the solvent in vacuo, saturated ammonium chloride was added, and the mixture was extracted with three portions of CH2C12. The combined organic phases were dried over MgS04 and evaporated in vacuo. The residue was purified by radial chromatography, eluting with 10% MeOH/CH2Cl2. Bicucullinediol (17e) was obtained in 73% yield (8 mg) from 11 mg of 2: [o]D +16.3°( c, 0.4, CHC13) (lit. -17°for the [S-(R*,S*)] isomer).18Adlumidinediol (17t) was obtained in 74% yield (14 mg) from 19 mg of 4: [a]D +25°(c 0.3, CHC13) (lit. -24°for the [S-(R*fl*)] isomer).18Acknowledgment. This work was generously supported by the National Institutes of Health: grant GM-37985 supported this work and grants RR-03351 and RR-04680 funded NMR and MS facilities, respectively. K.S.R. also thanks the University of Miami for a Maytag Fellowship.Supplementary Material Available: NMR spectra for compounds 2, 4-6, and 12-16 (18 pages). Ordering information is given on any current masthead page.

Synthesis, Characterization, and Theoretical Study of Sulfur-Containing Donor−Acceptor DCNQI Derivatives with Photoinduced Intramolecular Electron Transfer

“…The broad singlet at δ = 9.15 is again due to the fast isomerization of the NCN group adjacent to the sulfur atom and is assigned to H b . These assignments can be ascertained by comparison with the 1 H-NMR data previously reported for compound 14 for which the peri hydrogens appear at δ = 8.33 . Compounds 10 and 14 are therefore better represented by the structures displayed in Chart .…”

“…The synthesis of the N,N ‘-dicyano- p -quinonediimine derivatives 14 from the corresponding benzo[ b ]naphtho[2,3- e ][1,4]-dioxin-6,11-quinones ( 13 ) was previously described as intended donor−acceptor systems . No UV-vis data were reported.…”

Synthetic and Biological Utility of 2,3-Dichloro-1,4-Naphthoquinone: A Review

“…Scheme 39: Reaction of 2,3-dichloro-1,4-naphthoquinone (1) with oxygen nucleophiles. Compound 186 was synthesized in 25 to 87% yield by condensation of 2,3-dichloro-1,4naphthoquinone (1) with catechol and its derivatives (185) in the presence of pyridine as both base and solvent as shown in Scheme 39 [78].…”

N,N‘-Dicyanoquinone Diimines (DCNQIs): Versatile Acceptors for Organic Conductors

“…The DCNQIs 97 − 112 (Table , entries 93−108) were designed for donor effects from the heterocyclic residues. − They are accompanied by other heterocyclic DCNQI type acceptors ( 113 − 130 , entries 109− 126). Compounds 120 − 122 (entries 116−118) carrying cationic substituents, i.e., the corresponding radicals, are zwitterions …”

“…The DCNQIs 97-112 (Table 4, entries 93-108) were designed for donor effects from the heterocyclic residues. [37][38][39] They are accompanied by other heterocyclic DCNQI type acceptors (113-130, entries 109-…”