- Traceless Solid-Phase Synthesis of Trisubstituted Quinazolines
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(Chemical Equation Presented). A traceless polymer-supported synthesis of 4-benzoylquinazolines was developed using the following commercially available building blocks: Fmoc-α-amino acids, 2-nitrobenzensulfonyl chlorides and α-bromoacetophenones. The acy
- Fül?pov, Veronika,Cziesla, Lauren,Fleming, Megan,Lu, Yiwei,Voelker, Adrienne,Krchk, Viktor
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- Synthesis of indoles and quinazolines via additive-controlled selective C-H activation/annulation of N -arylamidines and sulfoxonium ylides
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Selective synthesis of indole and quinazoline products was achieved through a precise control of the C-H activation/annulation by changing the additives from NaOAc to CuF2/CsOAc. This strategy constructs indole and quinazoline scaffolds efficie
- Lai, Ruizhi,Wu, Xiaohua,Lv, Songyang,Zhang, Chen,He, Maoyao,Chen, Yuncan,Wang, Qiantao,Hai, Li,Wu, Yong
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p. 4039 - 4042
(2019/04/10)
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- Pd(0)-catalyzed benzylic arylation-oxidation of 4-methylquinazolines via sp3 C-H activation under air conditions
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An efficient and selective Pd(0)-catalyzed sp3 C-H bond arylation-oxidation of 4-methylquinazolines is reported. The method enables the introduction of arylketone at the benzylic position of 4-methylquinazolines without the use of an additional directing group, and atmospheric oxygen is used as the sole oxidant.
- Zhao, Dan,Zhu, Min-Xue,Wang, Yue,Shen, Qi,Li, Jian-Xin
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p. 6246 - 6249
(2013/09/23)
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- Catalytic action of azolium salts. IV. Preparations of 4-aroylquinazolines and 4-aroyl-1H-pyrazolo[3,4-d]pyrimidines by catalytic action of 1,3-dimethylimidazolium iodide
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The ability of 1,3-dimethylimidazolium iodide (1) to catalyze the aroylation of the chloroheteroarenes 4-8 with arenecarbaldehydes 3 as sources of the aroyl groups was examined in order to develop a preparative method of aroylheteroarenes. In the presence
- Miyashita,Matsuda,Suzuki,Iwamoto,Higashino
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p. 2017 - 2022
(2007/10/02)
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- Catalytic action of azolium salts. II. Aroylation of 4-chloroquinazolines with aromatic aldehydes catalyzed by 1,3-dimethylbenzimidazolium iodide
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When a mixture of 4-chloroquinazoline (7), an aromatic aldehyde 6, sodium hydride, and a catalytic amount of 1,3-dimethylbenzimidazolium iodide (1) in tetrahydrofuran (THF) was refluxed with stirring for an appropriate time, the chlorine atom of 7 was rep
- Miyashita,Matsuda,Iijima,Higashino
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- Reactions of 3-Benzoyl-3,4-dihydro-2-methyl-4-quinazolinecarbonitrile (2-Methylquinazoline Reissert Compound) with Acid, Base, Sodium Hydride, and Electrophiles
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Acid hydrolysis of 3-benzoyl-3,4-dihydro-2-methyl-4-quinazolinecarbonitrile (11, 2-methylquinazoline Reissert compound) resulted in the formation of the oxazole (13).Alkaline hydrolysis gave 2-methylquinazoline (12) and banzoic acid (8).The anion (D1), generated from 11 and NaH in dimethylformamide (DMF), underwent decomposition to give the ketone (14) and the cyanoquinazoline (15) together with by-products 12 and O-benzoylbenzoin (9).Compound 11 reacted with aromatic aldehydes (10a-c) in the presence of NaH to give the benzoates (16a-c) and by-products 12 and 15.Alkylation (or arylation) with alkyl (or aryl) halides (11a, b) afforded the corresponding 4-substituted derivatives (19a, b) and a by-product 14.The reactivities of 11 and 3-benzoyl-3,4-dihydro-4-quinazolinecarbonitrile (21, quinazoline Reissert compound) are compared. Keywords---Reissert compound; quinazoline; hydrolysis; Reissert compound anion; rearrengement; aromatization; electronic effect; electrophilic substitution
- Higashino, Takeo,Sato, Susumu,Suge, Hiroki,Tanji, Ken-Ichi,Miyashita, Akira,Katori, Tatsuhiko
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p. 930 - 939
(2007/10/02)
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