Efficient Synthesis of Aminonaphthoquinones and Azidobenzohydroquinones:  Mechanistic Considerations of the Reaction of Hydrazoic Acid with Quinones. An Overview

Couladouros, Elias A.; Plyta, Zoi F.; Haroutounian, Serkos A.; Papageorgiou, Vassilios P.

doi:10.1021/jo9614708

Cited by 60 publications

(45 citation statements)

References 45 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…Analogous transformations of 1,4-benzo- [11,12] and 1,4-naphthoquinones [11] were also observed in chloroform in an inert atmosphere.…”

mentioning

confidence: 64%

“…1a, 6a, X = Me; 2a, 7a, X = CF 3 mechanism proposed in [11] for the reaction of 1,4-naphthoquinone with sodium azide involved initial addition of azide ion to the quinone and subsequent aromatization of the ring. On the other hand, we previously found [15] that nucleophilic addition reactions of N-substituted 1,4-benzoquinone imines, in particular hydrohalogenation reactions, are initiated by protonation of the nitrogen atom with subsequent addition of halide ion (nucleophile).…”

mentioning

confidence: 99%

“…As shown above, heating of sulfonamides 6c-6e, 7c-7e, 15a, and 15b in boiling acetic acid or benzene leads to the formation of quinone imines 10c-10e, 11c-11e, 17a, and 17b as a result of intramolecular oxidation/reduction. Couladouros et al [11] proposed a mechanism for the formation of 2-azidonaphthalene-1,4-diol from sodium azide and 1,4-naphthoquinone with participation of acetic acid proton. It was also noted that intramolecular oxidation/reduction of analogous adduct derived from NaN 3 and 1,4-benzoquinone follows a similar scheme, though the reaction was carried out in an aprotic solvent under argon [11,12].…”

mentioning

confidence: 99%

See 2 more Smart Citations

Reaction of N-sulfonyl-1,4-benzoquinone imines with sodium azide

et al. 2016

View full text Add to dashboard Cite

Depending on the conditions and the order of addition of the reactants, reactions of N-sulfonyl-1,4benzoquinone imines with sodium azide afforded N-(3-azido-4-hydroxyphenyl)alkane(arene)sulfonamides, N-(3-azido-4-oxocyclohexa-2,5-dienylidene)alkane(arene)sulfonamides, and N-(3,5-diazido-4-hydroxyphenyl)alkanesulfonamides. Quantum chemical calculations showed that the reactions begin with addition of azide ion to the quinone imine.We previously synthesized new N-alkyl(trifluoromethyl)sulfonyl derivatives of 1,4-benzoquinone imine [1] and studied their reactivity toward potassium thiocyanate [1] and sodium arenesulfinates [2]. In the present work we examined reactions of these compounds with sodium azide.

show abstract

“…Analogous transformations of 1,4-benzo- [11,12] and 1,4-naphthoquinones [11] were also observed in chloroform in an inert atmosphere.…”

mentioning

confidence: 64%

mentioning

confidence: 99%

mentioning

confidence: 99%

See 1 more Smart Citation

Reaction of N-sulfonyl-1,4-benzoquinone imines with sodium azide

et al. 2016

View full text Add to dashboard Cite

show abstract

“…The evaluation of the redox chemistry and electrochemical properties of quinones isa useful way for identifying their biological evolutions. The constitution of substituted naphthoquinone compounds is a result of a Michael-type addition to 2,3-dichloro-1,4naphthoquinone (1) followed by chloride elimination to afford a quinonyl intermediate that then reacts with the related nucleophile to yield the final products [1][2][3]. Heterocyclic compounds bearing 1,4-naphthoquinones have long been the focus of synthetic chemistry due to their broad spectrum of applications in biological, pharmaceutical, and material science areas [4].…”

Section: Introductionmentioning

confidence: 99%

One-pot synthesis, characterization, and antioxidant capacity of sulfur- and oxygen-substituted 1,4-naphthoquinones and a structural study

et al. 2015

View full text Add to dashboard Cite

In the present study, we reported the onepot synthesis of S,S-and S,O-substituted 1,4-naphthoquinones, their structural studies, and investigation of their antioxidant activity. The multicomponent reactions of 2,3-dichloro-1,4-naphthoquinone with sulfur-and oxygencontaining nucleophiles were investigated to obtain highly functionalized S,S-and S,O-substituted 1,4-naphthoquinone derivatives. All new compounds were characterized on the basis of 1 H, 19 F, and 13 C nuclear magnetic resonance spectroscopy, mass spectrometry, and Fourier transform infrared spectroscopy. Crystal structure of 2,3-dihydro-2-(hydroxymethyl)naphtho[2,3-b]-1,4-oxathiin-5,10-dione was determined by X-ray diffraction method. The synthesized compounds were screened for their antioxidant capacity and free radical scavenging activity using the cupric reducing antioxidant capacity method and DPPH method, respectively. 3-Chloro-2-[3-(3-chloro-1,4-dihydro-1,4-dioxonaphthalen-2-yloxy)propylsulfanyl]-1,4-naphthoquinone shows the highest antioxidant capacity with 0.63 cupric reducing antioxidant capacity-trolox equivalent antioxidant capacity coefficient. Graphical abstract

show abstract

“…Hydrazoic acid as a 1,3-dipole chemical [2], which utilized in the synthesis of some important organic compounds [3][4][5][6][7] such as tetrazole [8], dephostatin [9], and key sulfoximine [10] obtained from reaction of hydrazoic acid or its derivatives with other chemicals.…”

Section: Introductionmentioning

confidence: 99%