146426-36-0Relevant academic research and scientific papers
Identification and isolation of insecticidal oxazoles from Pseudomonas spp.
Grundmann, Florian,Dill, Veronika,Dowling, Andrea,Thanwisai, Aunchalee,Bode, Edna,Chantratita, Narisara,Ffrench-Constant, Richard,Bode, Helge B.
, p. 749 - 752 (2012)
Two new and five known oxazoles were identified from two different Pseudomonas strains in addition to the known pyrones pseudopyronine A and B. Labeling experiments confirmed their structures and gave initial evidence for a novel biosynthesis pathway of t
First reported propylphosphonic anhydride (T3P) mediated Robinson–Gabriel cyclization. Synthesis of natural and unnatural 5-(3-indolyl)oxazoles
Szabó, Tímea,Dancsó, András,ábrányi-Balogh, Péter,Volk, Balázs,Milen, Mátyás
, p. 1353 - 1356 (2019/04/27)
In the present work, a propylphosphonic anhydride (T3P) assisted Robinson–Gabriel cyclization of N-acyl-β-oxotryptamines for the synthesis of 2-substituted-5-(3-indolyl)oxazoles has been developed. The reactions proceeded smoothly in acetonitri
A 5 - (3 - indolyl) - oxazole compound of preparation method
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Paragraph 0065; 0066; 0067; 0068, (2017/09/12)
The invention discloses a preparation method of a 5-(3-indolyl)-oxazole compound with a structure as shown in the formula (I). The method comprises the following step: in the presence of iodine and dimethyl sulfoxide, a compound with a structure as shown in the formula (II) and a compound with a structure as shown in the formula (III) undergo a contact reaction. Raw materials used in the preparation method are cheap and easily available. The preparation method is simple and the preparation step is short. In addition, the contact reaction can be carried out by a one kettle way during synthetic operation. Yield is high and can reach 84%. The preparation method provided by the invention is especially suitable for industrial production.
Palladium-catalyzed oxidative cross-coupling of azole-4-carboxylates with indoles: An approach to the synthesis of pimprinine
Zhou, Haipin,Gai, Kuo,Lin, Aijun,Xu, Jinyi,Wu, Xiaoming,Yao, Hequan
supporting information, p. 1243 - 1248 (2015/03/03)
An efficient and straightforward method for the production of 5-(3-indolyl)azoles incorporating the privileged structures indoles and azoles via palladium-catalyzed double C-H bond cleavage under mild conditions was disclosed. As expected, this protocol provided an easy method for the synthesis of indole alkaloids pimprinine and WS-30581 A in moderate yields. This journal is
One-pot total synthesis: The first total synthesis of chiral alkaloid pimprinol A and the facile construction of its natural congeners from amino acids
Xiang, Jiachen,Wang, Jungang,Wang, Miao,Meng, Xianggao,Wu, Anxin
supporting information, p. 7470 - 7475 (2014/12/10)
In this work, we accomplished the first total synthesis of chiral alkaloid pimprinol A and the facile construction of its natural congeners: pimprinine, pimprinethine, pimprinaphine, WS-30581A, WS-30581B, laboradorin 1, uguenenazole, balsoxine, texamine in one-pot from commercially available starting materials including amino acids. Further investigating into the mechanism revealed that this improved transformation was achieved by the integration of iodination, Kornblum oxidation, condensation, decarboxylation, annulation, and oxidation reaction sequence.
A novel and short synthesis of naturally occurring 5-(3′-indolyl) oxazoles
Kumar, Dalip,Sundaree, Swapna,Patel, Gautam,Kumar, Anil
experimental part, p. 1425 - 1428 (2011/02/22)
A novel, concise, and convenient synthesis of 5-(3′-indolyl)oxazoles using relatively benign reagent [hydroxy(2,4-dinitrobenzenesulfonyloxy)iodo] benezene has been described. The advantages of this procedure include operational simplicity, good yield, and
Synthesis of 5-(3-indolyl)oxazole natural products. Structure revision of Almazole D
Miyake, Fumiko,Hashimoto, Michinao,Tonsiengsom, Sorasaree,Yakushijin, Kenichi,Horne, David A.
experimental part, p. 4888 - 4893 (2010/08/06)
The synthesis and utility of β-oxotryptamine and β-oxytryptophan ester synthons provide a convenient entry to 5-(3-indolyl)oxazole natural products leading to a structure revision of almazole D.
Synthesis of oxazolylindolyl alkaloids via rhodium carbenoids
Doyle,Moody
, p. 1021 - 1022 (2007/10/02)
The oxazolylindole alkaloids pimprinine (1a), pimprinethine (1b) and WS-30581 A (1c) are readily obtained in two steps by rhodium(II) catalysed reaction of N-Boc-3-diazoacetylindole with the appropriate nitrile followed by removal of the Boc-group.
