1985-37-1Relevant articles and documents
One-pot syntheses of blue-luminescent 4-aryl-1H-benzo[f]isoindole-1, 3(2H)-diones by T3P activation of 3-arylpropiolic acids
Deni?en, Melanie,Kraus, Alexander,Reiss, Guido J.,Müller, Thomas J.J.
supporting information, p. 2340 - 2351 (2017/11/16)
In situ activation of 3-arylpropiolic acids with T3P (n-propylphosphonic acid anhydride) initiates a domino reaction furnishing 4-arylnaphtho[2, 3-c]furan-1, 3-diones in excellent yields. Upon employing these anhydrides as reactive intermediates blue-lumi
Room temperature cyclization of arylpropiolic acid anhydride: Synthesis of naphtho[2,3-c]furan-1,3-dione derivatives
Park, Jaerim,Kim, Ji Dang,Raja, Gabriel Charles Edwin,Choi, Hyun Chul,Lee, Sunwoo
supporting information, p. 1973 - 1979 (2017/10/17)
Cyclic anhydrides such as naphtho[2,3-c]furan-1,3-dione derivatives were synthesized from the reaction of arylpropiolic acids and 2-chloro-4,6-dimethoxy-1,3,5-triazine in the presence of N-methylmorpholine at room temperature. This mild condition provided
1-phenyl -2,3-naphthalene carboxylic acid anhydride, and its process for synthesis of derivatives of
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Paragraph 0010-0013, (2017/02/24)
The invention discloses a synthesis method of 1-phenyl-2,3-naphthalene dicarboxylic anhydride and derivatives thereof. The synthesis method is used for synthesizing the 1-phenyl-2,3-naphthalene dicarboxylic anhydride compounds under an alkali condition in
2,3-Dichloro-5,6-dicyano-para-benzoquinone (DDQ)/methanesulfonic acid (MsOH)-mediated intramolecular arene-alkene oxidative coupling
Kim, Ko Hoon,Lim, Cheol Hee,Lim, Jin Woo,Kim, Jae Nyoung
supporting information, p. 697 - 704 (2014/04/03)
An efficient intramolecular arene-alkene oxidative coupling of 1,4-diaryl-1,3-butadienes has been developed involving the use of a 2,3-dichloro-5,6-dicyano-para-benzoquinone (DDQ)/acid catalyst. The reaction involves the generation of a radical cation by abstraction of an electron from the substrate with DDQ, an intramolecular Friedel-Crafts-type reaction, and the loss of hydrogen radical.
Phthalocyanines and related compounds: XXXIX. Synthesis of derivatives of some substituted 1-phenylnaphthalene-2,3-dicarboxylic acids
Donyagina,Luk''yanets
, p. 795 - 799 (2007/10/03)
Derivatives (dinitriles, anhydrides, imides, N-phenylimides) of substituted 1-phenylnaphthalene-2,3-dicarboxylic and 1-phenylphenanthrene-2,3-dicarboxylic acids were prepared by the reactions of 2-bromomethylbenzophenones with various dienophiles. Starting from these derivatives, gallium complexes of substituted tetra-1-phenyl-2,3-naphthalocyanines and tetra(1-phenyl-2,3-phenanthro) porphyrazine were synthesized. 2005 Pleiades Publishing, Inc.
Unexpected thermal transformation of aryl 3-arylprop-2-ynoates: Formation of 3-(diarylmethylidene)-2,3-dihydrofuran-2-ones
Lellek, Vit,Hansen, Hans-Juergen
, p. 3548 - 3580 (2007/10/03)
A number of aryl 3-arylprop-2-ynoates 3 has been prepared (cf. Table 1 and Schemes 3-5). In contrast to aryl prop-2-ynoates and but-2-ynoates, 3-arylprop-2-ynoates 3 (with the exception of 3b) do not undergo, by flash vacuum pyrolysis (FVP), rearrangement to corresponding cyclohepta[b]furan-2(2H)-ones 2 (cf. Schemes 1 and 2). On melting, however, or in solution at temperatures >150% the compounds 3 are converted stereospecifically to the dimers 3-[(Z)-diarylmethylidene]-2,3-dihydrofuran-2-ones (Z)-11 and the cyclic anhydrides 12 of 1,4-diarylnaphthalene-2,3-dicarboxylic acids, which also represent dimers of 3, formed by loss of one molecule of the corresponding phenol from the aryloxy part (cf. Scheme 6). Small amounts of diaryl naphthalene-2,3-dicarboxylates 13 accompanied the product types (Z)-11 and 12, when the thermal transformation of 3 was performed in the molten state or at high concentration of 3 in solution (cf. Tables 2 and 4). The structure of the dihydrofuranone (Z)-11c was established by an X-ray crystal-structure analysis (Fig. 1). The structures of the dihydrofuranones 11 and the cyclic anhydrides 12 indicate that the 3-arylprop-2-ynoates 3, on heating, must undergo an aryl O → C(3) migration leading to a reactive intermediate, which attacks a second molecule of 3, finally under formation of (Z)-11 or 12. Formation of the diaryl dicarboxylates 13, on the other hand, are the result of the well-known thermal Diels-Alder-type dimerization of 3 without rearrangement (cf. Scheme 7). At low concentration of 3 in decalin, the decrease of 3 follows up to ca. 20% conversion first-order kinetics (cf. Table 5), which is in agreement with a monomolecular rearrangement of 3. Moreover, heating the highly reactive 2,4,6-trimethylphenyl 3-(4-nitrophenyl)prop-2-ynonate (3f) in the presence of a twofold molar amount of the much less reactive phenyl 3-(4-nitrophenyl)prop-2-ynonate (3g) led, beside (Z)-11f, to the cross products (Z)-11fg, and, due to subsequent thermal isomerization, (E)-11fg (cf. Scheme 10), the structures of which indicated that they were composed, as expected, of rearranged 3f and structurally unaltered 3g. Finally, thermal transposition of [17O]-3i with the 17O-label at the aryloxy group gave (Z)- and (E)-[17O2]-11i with the 17O-label of rearranged [17O]-3i specifically at the oxo group of the two isomeric dihydrofuranones (cf. Scheme 8), indicating a highly ordered cyclic transition state of the aryl O → C(3) migration (cf. Scheme 9).
6-Endo-Dig vs. 5-Exo-Dig Ring Closure in o-Hydroxyaryl Phenylethynyl Ketones. A New Approach to the Synthesis of Flavones and Aurones
Garcia, Hermenegildo,Iborra, Sara,Primo, Jaime,Miranda, Miguel A.
, p. 4432 - 4436 (2007/10/02)
The aryl phenylpropynoates 3a-c, prepared by esterification of phenylpropynoic acid with the corresponding phenols, by means of N,N'-dicyclohexylcarbodiimide, give upon irradiation the o-hydroxyaryl phenylethynyl ketones 4a-c.The cyclization of these compounds in basic media follows two alternative pathways: 6-endo-dig ring closure, to give the flavones 8a-c, and /or 5-exo-dig ring closure , to give the aurones 9a-c.The predominance of one or the other cyclization mode is strongly influenced by the reaction conditions.Thus, the use of potassium carbonate in acetoneas cyclizing reagent favors the 6-endo-dig process, while the 5-exo-dig process becomes clearly enhanced when using sodium ethoxide or potassium carbonate in ethanol.The mechanistic implications of these facts are discussed within the framework of Baldwin's rules.From the preparative point of view, the above results disclose the synthetic possibilities of the key ketones 4 as precursors of flavones and aurones.
Synthesis and Reactions of N-Hydroxy-1-phenylnaphthalene-2,3-dicarboximide
Baddawy, H. A.,Hamed, A. A.,El-Beih, A. A.,Metwally, R. N.
, p. 112 - 114 (2007/10/02)
1-Phenylnaphthalene-2,3-dicarboxylic anhydride (I) reacts with hydroxylamine hydrochloride to give N-hydroxy-1-phenylnaphthalene-2,3-dicarboximide (II) which on pyrolysis forms 1-phenylnaphthalene-2,3-dicarboximide (III).The imide III is also obtained by
