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    Home > Professor Song Qiuling's research group of Huaqiao University: furazan and isoxazole were synthesized by [2 + 1 + 1 + 1] cycloaddition reaction of thiogerate and tert butyl nitrite

    Professor Song Qiuling's research group of Huaqiao University: furazan and isoxazole were synthesized by [2 + 1 + 1 + 1] cycloaddition reaction of thiogerate and tert butyl nitrite

    • Last Update: 2019-07-08
    • Source: Internet
    • Author: User
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    Lead heterocyclic compounds are generally contained in many drugs, materials and bioactive molecules Furazan derivatives are important NO donors and have very important biological activities, such as anticancer, antibacterial, anti-inflammatory and so on In addition, isoxazole ring ranks 33rd in the 351 ring system of drugs on the market, which undoubtedly represents one of the most important skeletons in drugs and agricultural chemicals Recently, Professor Song Qiuling's research group of overseas Chinese University broke the traditional reaction form of sulfur oxide ylide For the first time, using multi-molecular sulfur ylide as carbene precursor and t Buono as nitrogen source, the valuable furazan containing two molecules of carbonyl and isoxazole containing three molecules of carbonyl were assembled through mild reaction way, which is of great significance in organic chemistry and pharmaceutical chemistry Relevant research results were published in organic letters (DOI: 10.1021/acs.orglett.9b01876) Professor Song Qiuling's research group was founded in May 2013, and was established as the new generation Institute of material transformation at the end of 2013 At present, there are one professor, two associate researchers, one lecturer, one administrative secretary, five doctors and 16 masters At present, it is mainly engaged in the research of organoboron chemistry, organometallic chemistry, free radical chemistry, organic fluorine chemistry, green chemistry and functional organic molecular synthesis Profile of Professor Song Qiuling: Professor Song Qiuling was selected into the National Youth millennium plan in 2012; he was selected into Xiamen high level talents and Quanzhou senior talents in 2013; in October 2013, overseas Chinese University established the Youth Federation, Professor Song Qiuling served as the vice chairman of the first committee of the Youth Federation, and was selected into the Fujian hundred talents plan in December 2013; 2014 In 2014, he was invited to be a young editorial board member of the Chinese chemistry letter, and was selected as a key talent in Xiamen As a leading talent, he established the material transformation and innovation team of overseas Chinese University, and was selected by the central organization department to participate in the "innovation ability training for young Chinese science and technology leaders" (two months) held in Shanghai and Sweden In 2015, he was selected as the top young talents of Quanzhou, in May 2015, he was selected as the "May 4th Youth Medal" of Fujian Province, in May 2015, he was selected as the vice president of Quanzhou Overseas Chinese Youth Federation; in 2016, he was awarded the Contribution Award (innovative talents) of Chinese overseas Chinese community, in 2016, he was awarded the youth science and technology award of Quanzhou City, in June 2016, he was invited as the vice president of Fujian new overseas Chinese talents Association In December 2016, he was elected as the executive director of Xiamen Federation of overseas Chinese; in December 2016, he was invited to become the Editorial Committee of China pharmaceutical industry journal; in December 2016, he was elected as the executive vice president of Fujian Overseas Chinese Youth Federation, vice president of overseas Chinese Federation of overseas Chinese University and the principal of Xiamen campus In June 2017, he was invited to be the vice president of Fujian new overseas Chinese Talent Association, and in August 2017, he was invited to be the member of the Standing Committee of Xiamen Overseas Chinese Association; in November 2018, he was awarded the Asian core program mechanization Award (Japan and Singapore) In January 2019, he was invited to be the deputy editor in chief of Journal of hetercyclic chemistry, and in May 2019, he was invited to be the editorial board member of Chinese chemistry letter Cutting edge scientific research achievements: furazan and isoxazole compounds were synthesized by [2 + 1 + 1 + 1] cycloaddition reaction of thioylide and tert butyl nitrite respectively In the past few years, researchers have proved that thioylide oxide is a general component for forging complex molecules in organic synthesis (Figure 1a) In particular, ylide is a prominent coupling partner in the transition metal catalyzed C-H activation, in which different guiding groups can achieve different aromatic and heterocyclic ketone functionalization Because of their bipolar nature, they can also be used as ketone precursors to provide a variety of ketones In addition to these transformations, the application of C-H cross coupling of thiophilides and thiophilides as weak guiding groups in the synthesis of substituted thiophilides has been occasionally reported Although great progress has been made in the research of sulfur ylide, most of the transformations involve only one molecule of sulfur oxide ylide As far as the author knows, the transformation of several sulfur oxide ylides has not been explored, and [2 + 1 + 1 + 1] cyclization of sulfonium oxide ylides has not been recorded so far Tbuono has become an excellent nitrogen source and can be used in the synthesis of N-heterocycles in organic synthesis As part of their continuing interest in t Buono and carbene chemistry, song Qiuling's group recently reported a novel [2 + 1 + 1 + 1] cyclization involving multiple molecules of sulfur oxide ylide They used matte ylide as carbene precursor and t Buono as nitrogen source to synthesize different furazan and isoxazole rings (Fig 1b) Fig 1 Reaction of sulfur oxide ylide (source: org Lett.) after determining the optimal reaction conditions, the author studied the substrate range of furazan 3 As shown in Figure 2, a series of sulfur oxide ylides with different electronic properties have been proved to be good carbene precursors (3a-3f), and the structure of 3C has been determined by X-ray single crystal diffraction In addition to para substituted aryl thiol ylides, ortho and meso substituted aryl thiol ylides are also well compatible in this transformation, and the target furazan 3g-3k can be obtained in quite high yield 1 and 1 m of ylide 1 were also good candidates for the reaction, and corresponding furazan (3 L and 3 m) were obtained It is also suitable for the cyclization of [2 + 1 + 1 + 1] to produce 3N The treatment of heterocyclic thioyelide (1o and 1P) with tbuono was also successful The required furazan 3O and 3P were obtained in high yield In addition to the aromatic thiofulide, lipofulide is a suitable carbene donor in this reaction, providing the expected furanone 3q and 3R, respectively Due to the competitive reaction among the molecules, it is challenging to obtain high yield isoxazole 4A through this new type of [2 + 1 + 1 + 1] cyclization Under the best reaction conditions of synthesizing isoxazole, the author also examined the substrate range of isoxazole As shown in Figure 3, many sulfur oxide ylides can provide the required isoxazole 4a-4d The structure of product 4A was clearly identified by X-ray single crystal diffraction Fig 2 Substrate range of furazan (source: org Lett.) Fig 3 Substrate range of isoxazole (source: org Lett.) the practicability of the scheme is illustrated by its application in situ transformation of furazan 3 When chloroform is used as solvent to carry out the reaction of sulfur ylide 1a, tert butyl nitrite 2 and norbornene 5 in one pot, the ((3a s, 4S, 7R, 7a s) - 3a, 4,5,6,7,7a-hexahydro-4,7-methylbenzo [D] isoxazol-3-yl) (phenyl) ketone 6 is obtained in medium yield (FIG 4A) In order to further transform furazan, furazan 3C was treated with ammonium hydroxide in MeOH, and (4-amino-1,2,5-oxadiazole-3-yl) (4-methoxyphenyl) - ketone 7 (Fig 4b) was prepared in 38% yield Figure 4 Application and transformation (source: org Lett.) was recently published on organizational letters (org Lett 2019, DOI: 10.1021/acs.orglett.9b01876) The corresponding author of this article is Professor Song Qiuling The first author of this article is Tang Zhonghe, a master student The author of this paper is: Zhonghe Tang, Yao Zhou and Qiu song * The above research work has been greatly supported by the "youth thousand" program of the Central Organization Department, general program of the National Natural Science Foundation, Fujian Natural Science Foundation, science and technology innovation and Leading Talents Program of Huaqiao University, Graduate Innovation Fund of Huaqiao University, etc A review of previous reports: research group of Professor Song Qiuling of Huaqiao University: copper catalyzed ring opening reaction of 3-aminoindazole Nowadays, people and scientific research have been paid more and more attention in the economic life China has ushered in the "node of science and technology explosion" Behind the progress of science and technology is the work of countless scientists In the field of chemistry, in the context of the pursuit of innovation driven, international cooperation has been strengthened, the influence of Returned Scholars in the field of R & D has become increasingly prominent, and many excellent research groups have emerged in China For this reason, CBG information adopts the 1 + X reporting mechanism CBG information, chembeangoapp, chembeango official microblog, CBG wechat subscription number and other platforms jointly launch the column of "people and scientific research", approach the domestic representative research group, pay attention to their research, listen to their stories, record their demeanor, and explore their scientific research spirit.
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