74048-04-7Relevant articles and documents
Synthesis of 2,5-Disubstituted Oxazoles from Arylacetylenes and α-Amino Acids through an i 2 /Cu(NO 3) 2 ?3H 2 O-Assisted Domino Sequence
Wang, Jungang,Cheng, Yan,Xiang, Jiachen,Wu, Anxin
supporting information, p. 743 - 747 (2019/03/26)
A new strategy has been developed for the synthesis of 2,5-disubstituted oxazoles from easily available arylacetylenes and α-amino acids in the presence of Cu(NO 3) 2 ?3H 2 O and iodine. This reaction process involves the I 2 /Cu(NO 3) 2 ?3H 2 O-assisted transformation of arylacetylene to α-iodo acetophenone, Kornblum oxidation to phenylglyoxal, condensation to imine, decarboxylation/annulation/oxidation reaction sequence to approach 2,5-disubstituted oxazoles.
4 - Substituted benzene sulfonamide derivative and its preparation method and application
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Paragraph 0201-0204; 0205-0208, (2018/04/21)
The present invention discloses a class of new 4-substituted benzene sulfonamide derivatives represented by a formula (I), wherein the 4-substituted benzene sulfonamide derivatives have good antitumor activity, and each group is defined in the specification. The present invention further discloses a preparation method of the derivative, a pharmaceutical composition containing the derivative, and applications of the 4-substituted benzene sulfonamide derivative and the pharmaceutical composition containing the derivative as the antitumor drug. The formula I is defined in the specification.
A Heterogeneous Gold(I)-Catalyzed [2 + 2 + 1] Annulation of Terminal Alkynes, Nitriles, and Oxygen Atoms Leading to 2,5-Disubstituted Oxazoles
Yang, Weisen,Zhang, Rongli,Yi, Feiyan,Cai, Mingzhong
, p. 5204 - 5211 (2017/05/24)
The first heterogeneous gold(I)-catalyzed [2 + 2 + 1] annulation of terminal alkynes, nitriles, and oxygen atoms has been achieved by using an MCM-41-immobilized phosphine-gold(I) complex as catalyst and 8-methylquinoline N-oxide as oxidant under mild conditions, yielding a variety of 2,5-disubstituted oxazoles in good to excellent yields with broad substrate scope. The new heterogeneous gold(I) catalyst can easily be recovered by simple filtration of the reaction solution and recycled for at least eight times without significant loss of activity.
METHOD FOR PRODUCING OXAZOLE COMPOUND
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Paragraph 0049;0053-0054, (2016/10/10)
PROBLEM TO BE SOLVED: To provide a method for producing an oxazole compound which makes it possible to obtain an oxazole compound inexpensively and safely. SOLUTION: A ketone compound, a nitrile compound, an iodinating agent, an oxidizing agent and an acid catalyst are mixed for a reaction to obtain an oxazole compound. SELECTED DRAWING: Figure 1 COPYRIGHT: (C)2016,JPOandINPIT
Metal-Free sp3 C-H Functionalization: PABS/I2-Promoted Synthesis of Polysubstituted Oxazole Derivatives from Arylethanones and 2-Amino-2-alkyl/arylacetic Acid
Hu, Ting,Yan, Hao,Liu, Xingxing,Wu, Chaoyang,Fan, Yuxing,Huang, Jing,Huang, Guosheng
supporting information, p. 2866 - 2869 (2015/12/18)
A nonmetal-catalyzed process for the synthesis of polysubstituted oxazoles from inexpensive and readily available α-amino acids and methyl ketones is established. This reaction is proposed to achieve oxidative cleavage of C(sp3)-H bonds, followed by decarboxylation and annulation. The mild reaction conditions employed in both cases enable the tolerance of a wide range of functional groups as well as high reaction efficiency.
One-pot preparation of 2,5-disubstituted and 2,4,5-trisubstituted oxazoles from aromatic ketones with molecular iodine, oxone, and trifluoromethanesulfonic acid in nitriles
Imai, Sho,Kikui, Hiroki,Moriyama, Katsuhiko,Togo, Hideo
, p. 5267 - 5274 (2015/07/15)
Alkyl aryl ketones were successfully converted into the corresponding 2,5-disubstituted and 2,4,5-trisubstituted oxazoles in good to moderate yields in a one-pot manner, utilizing iodine, Oxone, and trifluoromethanesulfonic acid in nitriles under transition-metal-free conditions. The present method could be used for the preparation of Oxaprozin from benzyl phenyl ketone and succinonitrile. A possible reaction mechanism was proposed in which the key intermediates were α-iodoalkyl aryl ketones and α-iodosylalkyl aryl ketones.
Direct synthesis of 2,5-disubstituted oxazoles through an iodine-catalyzed decarboxylative domino reaction
Xu, Wei,Kloeckner, Ulrich,Nachtsheim, Boris J.
, p. 6065 - 6074 (2013/07/26)
An efficient iodine-catalyzed synthesis of highly substituted oxazoles is presented. Starting from readily available aryl methyl ketones, β-keto esters, or styrenes, in combination with α-amino acids as amine-containing coupling partners, the corresponding 2-alkyl-5-aryl- substituted oxazoles were obtained in up to 80% yield via a decarboxylative domino reaction.
Iodoarene-catalyzed one-pot preparation of 2,4,5-trisubstituted oxazoles from alkyl aryl ketones with mCPBA in nitriles
Kawano, Yuhta,Togo, Hideo
experimental part, p. 6251 - 6256 (2011/03/19)
2,4,5-Trisubstituted oxazoles could be easily prepared in moderate yields by the reaction of alkyl aryl ketones, iodoarene, m-chloroperbenzoic acid, and trifluoromethanesulfonic acid in acetonitrile, propionitrile, butyronitrile, and isobutyronitrile, res
Iodoarene-mediated one-pot preparation of 2,5-disubstituted and 2,4,5-trisubstituted oxazoles from alkyl aryl ketones with oxone in nitriles
Ishiwata, Yoshihide,Togo, Hideo
experimental part, p. 10720 - 10724 (2010/03/01)
The reaction of alkyl aryl ketones with Oxone and trifluoromethanesulfonic acid in the presence of iodoarene in acetonitrile, propionitrile, butyronitrile, and isobutyronitrile, provided directly the corresponding 2,5-disubstituted and 2,4,5-trisubstituted oxazoles, respectively, in moderate yields. Here, reactive aryliodonium I(III) species is formed in situ by the reaction of iodoarene with Oxone and trifluoromethanesulfonic acid, and the formed aryliodonium I(III) species reacts with alkyl aryl ketone to generate β-keto iodonium species. Then, β-keto iodonium species reacts with nitrile to produce the corresponding oxazole. In principle, iodoarene works as a catalyst. However, 1 equiv of iodoarene is required because 1 equiv of reactive aryliodonium I(III) species must be formed before the reaction with alkyl aryl ketone.
Hypervalent iodine(III) mediated synthesis of 2-substituted-5-aryloxazoles
Kang, Iou-Jiun,Wang, Huey-Min,Lin, Mei-G,Chen, Ling-Ching
, p. 1031 - 1034 (2007/10/03)
A direct and efficient method for the preparation of 2-substituted-5- aryloxazoles was realized by reaction of aryl methyl ketones with various nitriles in the presence of phenyliodine(III) triflate.