- Benzopyrazinoisoindigo or Its Reduced Form? Synthesis, Clarification, and Application in Field-Effect Transistors
-
Benzopyrazinoisoindigo, a pigment reported 40 years ago, should be a good candidate for n-type semiconductors if the reported structure is correct. Reinvestigation of this molecule revealed that it is actually (4H,4′H)-benzopyrazinoisoindigo, which could be considered as the reduced form of benzopyrazinoisoindigo, and hence, it is a good candidate for p-type semiconductors. The route toward the synthesis of this molecule was optimized, and a mechanism was accordingly proposed. A field-effect transistor based on this material showed a hole mobility up to 2.5 × 10-2 cm2 V-1 s-1. An expedient route for the synthesis of unexpectedly alkylated (4H,4′H)-benzopyrazinoisoindigo is developed, which also clarifies the previously reported structure. A mechanism is accordingly proposed. A field-effect transistor based on this material shows a hole mobility up to 2.5 × 10-2 cm2 V-1 s-1.
- Wang, Xiao,Zhao, Zhiyuan,Ai, Na,Pei, Jian,Liu, Yunqi,Wan, Xiaobo
-
-
Read Online
- Preparation method, preparation device and intermediate of 4 -chlorophthalic anhydride
-
The invention discloses a preparation method of 4 -chlorophthalic anhydride, a preparation device and an intermediate. The preparation method comprises the following steps: 2, 3 - dichloro maleic anhydride and 2 - chlorine -1, 3 - butadiene takes place cyclization reaction to obtain 1, 2 and 4 - trichloroacetic anhydride. Reaction of the 1, 2 and 4 - trichloroalternative dihydrophthalic anhydride in the removal HCl results in 4 -chlorophthalic anhydride. The chlorination reaction of maleic anhydride and thionyl chloride under the conditions of pyridine catalysts gives the 2, 3 -dichloromaleic anhydride. By adopting 2, 3 -dichloromaleic anhydride and 2 - chlorine -1, 3 - butadiene takes place D-A cyclization reaction, HCl-chlorophthalic anhydride is synthesized with high selectivity, and the 4 - 4 -chlorophthalic anhydride process disclosed by the invention realizes continuous production.
- -
-
Paragraph 0084-0092; 0108-0111; 0117-0120; 0126-0129; ...
(2021/10/27)
-
- First Stereoselective Total Synthesis of a Dimeric Naphthoquinonopyrano-γ-lactone: (+)-γ-Actinorhodin
-
We have accomplished the first total synthesis of an isomerically pure naphthoquinonopyrano-γ-lactone dimer, γ-actinorhodin, in eleven steps. Two steps exploit pairs of peri-MeO groups as unusual selectivity controls. The respective MeO groups convey the steric bulk of a bromo or iodo substituent located ortho to one MeO group as steric hindrance into the vicinity of the second MeO group. This relay effect was indispensable for exerting regiocontrol in an aromatic bromination and diastereocontrol in an oxa-Pictet–Spengler cyclization. The absolute configuration of our target compound was established in an asymmetric Sharpless dihydroxylation of a β,γ-unsaturated ester, which was synthesized in a Heck coupling of a bromoiodonaphthalene with ethyl vinylacetate. The dihydroxylation provided the γ-hydroxylactone moiety of the bromonaphthalene that was used as the substrate in the oxa-Pictet–Spengler cyclization. Dimerization to the core of γ-actinorhodin occurred by two Suzuki couplings.
- Neumeyer, Markus,Brückner, Reinhard
-
supporting information
p. 3383 - 3388
(2017/03/17)
-
- With anticancer activity of 3, 4 - b (3 - indole) - 2, 5 - dione - 1 - pyrrole thiourea compound and its preparation method and application
-
The invention discloses a 3,4-bi(3-benzpyrole)-2,5-dione-1-pyrroleimine thiourea compound with antitumor activity and a preparation method and application thereof. The technical scheme of the invention is characterized in that the 3,4-bi(3-benzpyrole)-2,5-dione-1-pyrroleimine thiourea compound with antitumor activity is prepared by taking a substituted isothiocyanate compound R-NCS and 1-amino-3,4-bi(3-benzpyrole)-3-pyrroline-2,5-dione shown in the specification as raw materials, and the structural general formula is shown in the specification. The invention further discloses the preparation method and the antitumor activity of the 3,4-bi(3-benzpyrole)-2,5-dione-1-pyrroleimine thiourea compound with antitumor activity. The preparation method disclosed by the invention has the advantages that the raw material is low in price and easily available, the operation is simple, and the prepared 3,4-bi(3-benzpyrole)-2,5-dione-1-pyrroleimine thiourea compound has better biological activity, and has better application prospect in preparation of antitumor medical compounds.
- -
-
Paragraph 0033; 0034; 0035; 0036; 0037
(2017/08/25)
-
- Indole [2,3-a] pyrrole[3,4-c] carbazole-5,7-diketone-6-thiosemicarbazone compounds with antitumor activity as well as preparation method and application of compounds
-
The invention discloses indole [2,3-a] pyrrole[3,4-c] carbazole-5,7-diketone-6-thiosemicarbazone compounds with antitumor activity as well as a preparation method and an application of the compounds. The technical scheme is characterized in that the indole [2,3-a] pyrrole[3,4-c] carbazole-5,7-diketone-6-thiosemicarbazone compounds with the antitumor activity are prepared from raw materials including substituent isothiocyanate compounds R-NCS and 6-amino-indole [2,3-a] pyrrole[3,4-c] carbazole-5,7-diketone shown in the specification and has a general structure formula shown in the specification. The invention further discloses the preparation method of the indole [2,3-a] pyrrole[3,4-c] carbazole-5,7-diketone-6-thiosemicarbazone compounds with the antitumor activity and the application of the indole [2,3-a] pyrrole[3,4-c] carbazole-5,7-diketone-6-thiosemicarbazone compounds with the antitumor activity in preparation of an antitumor drug. According to the preparation method, the raw materials are cheap and easy to obtain, the operation is simple, and the prepared indole [2,3-a] pyrrole[3,4-c] carbazole-5,7-diketone-6-thiosemicarbazone compounds have better biological activity and have better application prospect in preparation of an antitumor drug compound.
- -
-
Paragraph 0045; 0046; 0047; 0048; 0049
(2017/04/03)
-
- 3. 4 - b (3 - indole) - 2, 5 - dione -3 - pyrroline imine compound and its preparation method and application
-
The invention discloses a 3,4-bi(3-indole)-2,5-dione-3-pyrrolineimine compound, a preparation method of the compound and application of the compound in an anti-cancer drug. The key points of the technical scheme are that the 3,4-bi(3-indole)-2,5-dione-3-pyrrolineimine compound is prepared by taking an aldehyde compound R-CHO and 1-amino-3,4-bi(3-indole)-3-pyrroline-2,5-dione with the structural formula which is as shown in the specification as raw materials; and the general structural formula of the compound is as shown in the specification. The invention also discloses a method for preparing the 3,4-bi(3-indole)-2,5-dione-3-pyrrolineimine compound and application of the compound in the anti-cancer drug. According to the preparation method disclosed by the invention, the raw materials are low in price and readily available, the operation is simple, and the prepared 3,4-bi(3-indole)-2,5-dione-3-pyrrolineimine compound has high biological activity and has good application prospects in the preparation of anti-cancer drug compounds.
- -
-
Paragraph 0037; 0038; 0039; 0040; 0041
(2017/07/25)
-
- Indolo[2, 3-a]pyrrole[3, 4-c]carbazole-5, 7-dione-6-arylhydrazone compound and its preparation method and use in anti-cancer drug
-
The invention discloses an indolo[2, 3-a]pyrrole[3, 4-c]carbazole-5, 7-dione-6-arylhydrazone compound and its preparation method and use. The indolo[2, 3-a]pyrrole[3, 4-c]carbazole-5, 7-dione-6-arylhydrazone compound is prepared from an aldehyde compound R-CHO and 6-amino-indolo[2, 3-a]pyrrole[3, 4-c]carbazole-5, 7-dione as raw materials and has a general structural formula shown in the description. The invention also discloses a preparation method of the indolo[2, 3-a]pyrrole[3, 4-c]carbazole-5, 7-dione-6-arylhydrazone compound and a use of the indolo[2, 3-a]pyrrole[3, 4-c]carbazole-5, 7-dione-6-arylhydrazone compound in preparation of anti-cancer drugs. The preparation method has the advantages of easily available raw materials and simple processes. The indolo[2, 3-a]pyrrole[3, 4-c]carbazole-5, 7-dione-6-arylhydrazone compound has good biological activity and has a good application prospect in preparation of anti-cancer drug compounds.
- -
-
Paragraph 0045; 0046; 0047; 0048; 0049
(2017/08/28)
-
- DDQ-mediated oxidative coupling: An approach to 2,3-dicyanofuran (thiophene)
-
A facile oxidative coupling of α-carbonyl radicals to 2,3-dichloro-5,6-dicyanobenzoquinone (DDQ) for the synthesis of 2,3-dicyanofurans and thiophenes starting from readily available β-diketones, simple ketones, and β-keto thioamides in up to 95% yield in one step was developed. Mechanistic investigations revealed that a radical process could be involved in this transformation, and a water promoted C-C bond cleavage pathway is proposed for the formation of 2,3-dicyanofurans and thiophenes.
- Wang, Zheng-Lin,Li, Hong-Liang,Ge, Li-Shi,An, Xing-Lan,Zhang, Zi-Gang,Luo, Xiaoyan,Fossey, John S.,Deng, Wei-Ping
-
supporting information
p. 1156 - 1165
(2014/03/21)
-
- Synthesis and biological evaluation of 3-chloro-4-(indol-3-yl)-2,5- pyrroledione derivatives as antitumor agents
-
A series of 3-chloro-4-(indol-3-yl)-2,5-pyrroledione derivatives were synthesized and evaluated for their cytotoxic activities in vitro against five human cancer cell lines (K562, A549, ECA-109, KB and SMMC-7721). Most compounds displayed potent cytotoxicity with IC50 values in low micromolar range. The results showed that the existence of the chlorine atom at 3-position on the pyrroledione ring was crucial for the activity. Compound 6a, the most potent one (IC50: 0.67～3.93 μM), would be a promising template for further development of novel antitumor agents.
- Lin, Yuchen,Chen, Jing
-
p. 382 - 389
(2013/07/26)
-
- Synthetic Approaches to Chlorinated 5-Hydroxy-5-Methyl-2-Furanones
-
The syntheses of chlorinated 5-hydroxy-furanones with a mono-, di-, and trichloromethyl group at C-5 are described.The 5-chloromethyl hydroxyfuranones were obtained by chlorination of levulinic acid followed by triethylamine promoted elimination of hydrogen chloride.Hydrolyses of chlorinated 4-cyclopentene-1,3-diones yielded 5-dichloromethyl hydroxyfuranones.The trichloromethyl group was incorporated to maleic anhydride through thermal decomposition of sodium trichloroacetate.
- Franzen, Robert,Kronberg, Leif
-
p. 10945 - 10958
(2007/10/02)
-
- ASYMMETRIC HYDROGENATION CATALYZED BY RHODIUM COMPLEXES OF 2,3-BIS(DIMENTHYLPHOSPHINO)MALEIC ANHYDRIDE AND 2,3-BIS(DIMENTHYLPHOSPHINO)-N-PHENYLMALEIMIDE
-
2,3-Bis(dimenthylphosphino)maleic anhydride and the phenylimide derivative have been prepared from 2,3-dichloromaleic anhydride and 2,3-dichloro-N-phenylmaleimide, respectively, and dimenthyl(trimethylsilyl)phosphine.These compounds have been used as ligands for Rh complexes and have been tested in the asymmetric hydrogenation of α-acetamidocinnamic acid, methyl-α-acetamidocinnamate and itaconic acid.Optical yields of up to approximately 70percent were obtained with α-acetamidocinnamic acid.
- Kinting, Annegret,Krause, Hans-Walter
-
p. 259 - 264
(2007/10/02)
-
- NEW REACTIONS OF 4,5-DICHLORO-2-DICHLOROMETHYLENE-4-CYCLOPENTENE-1,3-DIONE
-
The reaction of 4,5-dichloro-2-dichloromethylene-4-cyclopentene-1,3-dione with DMFA gives a high yield of 2,3-dichloro-5-(dimethyliminiomethyl)-2-cyclopentene-1,4-dione. 2,3-Dichloro-5,5-bismethylthio-2-cyclopentene-1,4-dione was isolated as a result of the analogous reaction with DMSO.A reaction mechanism involving diketocarbene is proposed.
- Gunbin, V. N.,Talzi, V. P.,Gudoshnikov, S. K.,Barysheva, N. A.,Maslennikov, E. I.
-
p. 465 - 468
(2007/10/02)
-
- UNKNOWN REACTIONS OF POLYCHLORINATED CYCLOPENTENONES WITH DIMETHYL SULFOXIDE
-
It was shown that perchloro-2-cyclopenten-1-one, perchloro-2-cyclopentene-1,4-dione, perchloro-2,5-dihydrofuran-2-one, perchloroindenone, and 2,3,4,4,5-pentachloro-2-cyclopenten-1-one enter into the Pummerer reaction with dimethyl sulfoxide like acid chlorides.
- Maslennikov, E. I.,Talzi, V. P.,Gunbin, V. N.,Yasman, Ya. B.,Gudoshnikov, S. K.
-
p. 2258 - 2260
(2007/10/02)
-
- Method of preparing dichloromaleic anhydride
-
To prepare dichloromaleic anhydride, hexachlorobutadiene is subjected to oxidation with sulfur trioxide at a temperature ranging from 10 to 110° C in the presence of iodine or an iodine-containing compound such as an alkali metal iodide, whereafter the desired product is separated from the reaction mass. The method of the present invention makes it possible to increase the yield of dichloromaleic anhydride up to 96% by weight, whereas in the prior art methods it is 80% by weight at most; the reaction time in the method according to the present invention is reduced by about 10 times as compared to that of the prior art methods.
- -
-
-
