1122-17-4Relevant articles and documents
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McDonald,R.N.,Krueger,R.A.
, p. 2542 - 2544 (1963)
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Benzopyrazinoisoindigo or Its Reduced Form? Synthesis, Clarification, and Application in Field-Effect Transistors
Wang, Xiao,Zhao, Zhiyuan,Ai, Na,Pei, Jian,Liu, Yunqi,Wan, Xiaobo
, p. 2603 - 2607 (2016)
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.
First Stereoselective Total Synthesis of a Dimeric Naphthoquinonopyrano-γ-lactone: (+)-γ-Actinorhodin
Neumeyer, Markus,Brückner, Reinhard
supporting information, p. 3383 - 3388 (2017/03/17)
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.
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
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Paragraph 0045; 0046; 0047; 0048; 0049, (2017/04/03)
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.