In Situ Generation of Quinolinium Ylides from Diazo Compounds: Copper-Catalyzed Synthesis of Indolizine

Chen, Rongxiang; Zhao, Yiming; Sun, Hongjian; Shao, Ying; Xu, Yudong; Ma, Min; Ma, Liang; Wan, Xiaobing

doi:10.1021/acs.joc.7b01042

Cited by 61 publications

(20 citation statements)

References 79 publications

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“…Traditional synthetic routes to indolizines mainly comprise the Scholtz or Chichibabin reactions. More recently, cycloaddition reactions (1,3‐dipolar cycloadditions), intramolecular cyclizations using acetic anhydride, formation of C3–C4 bond, formation of C1–C9 bond, and formation of C8–C9 bond have been reported . However, most of these methods suffer from some drawbacks, such as the formation of conjugate‐acid waste, narrow substrate scope, harsh reaction conditions, need for toxic transition‐metal catalysts and harmful organic solvents.…”

Section: Methodsmentioning

confidence: 99%

Hemoglobin‐Catalyzed Synthesis of Indolizines Under Mild Conditions

Tang

et al. 2019

Eur J Org Chem

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Hemoglobin-catalyzed synthesis of indolizines via a multicomponent reaction has been reported for the first time. The corresponding indolizines were obtained in moderate to high yields by using this method. This mild, efficient and practical method is distinguished by the use of a commercially inex-Indolizines, a class of heteroaromatic compounds containing two condensed rings (5-and 6-membered) and a bridging nitrogen atom, have been widely applied in natural products and synthetic pharmaceuticals. [1,2] These types of compounds have also been applied as dyes and biological markers due to their photophysical properties. [3][4][5][6][7] Therefore, the development of efficient methods for the synthesis of indolizines continues to attract the attention of organic chemists. Traditional synthetic routes to indolizines mainly comprise the Scholtz or Chichibabin reactions. More recently, cycloaddition reactions (1,3-dipolar cycloadditions), intramolecular cyclizations using acetic anhydride, formation of C3-C4 bond, formation of C1-C9 bond, and formation of C8-C9 bond have been reported. [8][9][10][11][12][13][14] However, most of these methods suffer from some drawbacks, such as the formation of conjugate-acid waste, narrow substrate scope, harsh reaction conditions, need for toxic transition-metal catalysts and harmful organic solvents. Thus, an environmentally preferable and efficient method to synthesize indolizines for practical applications must be developed.Biocatalysis is a highly attractive strategy in organic synthesis for organic synthesis due to its efficient, selective and environment-friendly characteristics. [15] A new biocatalytic approach relies on the promiscuity of enzymes to catalyze reactions that are different than their native functions. This interesting property of protein allows chemists to explore new types of biocatalytic organic reactions and dramatically expands the application of catalytic proteins within the field of organic chemistry. [16][17][18][19][20][21][22] [a]

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Section: Methodsmentioning

confidence: 99%

Hemoglobin‐Catalyzed Synthesis of Indolizines Under Mild Conditions

Tang

et al. 2019

Eur J Org Chem

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“…In 2017, Wan et al reported a Cu-catalyzed one-pot reaction for a simple construction of indolizine derivatives with quinolines, diazo compounds and electrophilic alkenes (Scheme 13). [26] A variety of diazoesters 33 were well tolerated under this catalytic system along with 71 examples under mild conditions in open air. In their mechanism study, the initially formed adduct 39 a rather than product 40 a was detected by LC-MS and intermediate 39 a was isolated in 56% yield when the control reaction was conducted under a N 2 atmosphere (Scheme 13, bottom part).…”

Section: Cu-catalyzed [3 + 2]-cycloadditionmentioning

confidence: 95%

[3+2]‐Cycloaddition of Catalytically Generated Pyridinium Ylide: A General Access to Indolizine Derivatives

Dong

2020

Asian J Org Chem

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Pyridinium ylide is a versatile building block in synthetic organic chemistry, especially in the synthesis of N‐heterocycles. In this minireview, we have summarized the advances of [3+2]‐cycloaddition of catalytically generated pyridinium ylide for the synthesis of indolizines (since 1970s). Accordingly, the ylide discussed in this article is generated in situ from carbene precursors and N‐heteroarenes under catalytic conditions, including photocatalysis/thermocatalysis, and metal‐catalysis. The metal‐catalyzed version is the main focus, which is classified and summarized based on the type of dipolarophiles, alkyne and alkene, each class is further subdivided according to the metal catalysts used in these reactions. The analogous [3+2]‐cycloaddition of vinyl metal carbene with pyridines, the formation of pyridinium ylide with other type of carbene precursors or with different N‐heteroarenes, have been also included herein separately.

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“…Oxime acetate (45) was used with toluene derivatives (Scheme 17), which produced trisubstituted pyridine 47. [31] Benzylamine and p-toluenesulfonylhydrazone could also furnish the desired product when used as a substitute for toluene.…”

Section: Pyridine Synthesismentioning

confidence: 99%

“…Wan and co-workers reported indolizine formation by in situ generated quinolium ylides from diazo compounds (Scheme 31b). [45] This three-component reaction proceeds through a copper carbene species which forms pyridinium ylide intermediate.…”

Section: Indolizine Synthesismentioning

confidence: 99%

Copper in Efficient Synthesis of Aromatic Heterocycles with Single Heteroatom

Pal

Lahiri

2020

Eur J Org Chem

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Aromatic heterocycles are important structural units in various naturally occurring compounds. Its abundance has drawn attention of synthetic chemists for decades. In the current scenario, new methodologies employing cheap transition metal reagents are highly desirable for efficient and practical synthesis of heterocyclic compounds. In this review article, strategies to synthesize aromatic heterocycles by inexpensive copper reagents have been discussed.

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In Situ Generation of Quinolinium Ylides from Diazo Compounds: Copper-Catalyzed Synthesis of Indolizine

Cited by 61 publications

References 79 publications

Hemoglobin‐Catalyzed Synthesis of Indolizines Under Mild Conditions

Hemoglobin‐Catalyzed Synthesis of Indolizines Under Mild Conditions

[3+2]‐Cycloaddition of Catalytically Generated Pyridinium Ylide: A General Access to Indolizine Derivatives

Copper in Efficient Synthesis of Aromatic Heterocycles with Single Heteroatom

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