Hemoglobin: A New Biocatalyst for the Synthesis of 2‐substituted Benzoxazoles <i>via</i> Oxidative Cyclization

Li, Fengxi; Li, Zhengqiang; Tang, Xuyong; Cao, Xinyu; Wang, Chunyu; Li, Jialin

doi:10.1002/cctc.201801760

Cited by 20 publications

(7 citation statements)

References 41 publications

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“…Hemoglobins, the most abundant hemoproteins in all groups of organisms, are ideal biocatalysts because of their low cost, commercial availability and good stability. Most studies to date have focused on using hemoglobins to catalyze traditional oxidation reactions and not have found widespread use in catalyzing new types of organic reactions . As part of our studies on the development of hemoprotein‐catalyzed organic reactions, we focused on the synthesis of indolizines catalyzed by hemoglobin via a multicomponent reaction (Scheme ).…”

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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“…Recently, enzyme catalytic promiscuity, the ability of a single active site of enzyme to catalyze new types of reactions that are different from natural ones, has been developed to widen the application of enzyme in organic synthesis. [22][23][24][25][26] In this area, lipases demonstrate the outstanding catalytic promiscuous abilities for their excellent stability and broad specificity, and many elegant works have been reported. [27][28][29][30][31][32][33][34][35][36][37][38][39][40][41][42][43][44][45] As a further study to develop new types of organic reactions catalyzed by lipase, we reported here an efficient and mild method for the synthesis of N′-alkyl benzohydrazides (Scheme 1).…”

Section: S C H E M E 1 Synthesis Of N′-alkyl Benzohydrazides Catalyze...mentioning

confidence: 99%

“…Therefore, it remains necessary to develop a safer and mild reaction method for efficient synthesis of benzohydrazides. Recently, enzyme catalytic promiscuity, the ability of a single active site of enzyme to catalyze new types of reactions that are different from natural ones, has been developed to widen the application of enzyme in organic synthesis 22–26 . In this area, lipases demonstrate the outstanding catalytic promiscuous abilities for their excellent stability and broad specificity, and many elegant works have been reported 27–45 .…”

Section: Introductionmentioning

confidence: 99%

Lipase‐catalyzed hydrazine insertion for the synthesis of N′‐alkyl benzohydrazides

et al. 2022

Biotech and App Biochem

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N′-alkyl benzohydrazides are classic organic compounds that have been widely utilized in organic chemistry. In this study, an efficient method was developed for the synthesis of N′-alkyl benzohydrazides by hydrazine insertion catalyzed by lipase. Under the optimal conditions (Morita-Baylis-Hillman ketone [1 mmol], phenylhydrazine [1.3 mmol], N,N-dimethylformamide [2 ml], lipase [20 mg], room temperature, 12 h), satisfactory yields (71-97%) and substrate tolerance were obtained when porcine pancreatic lipase was used as biocatalyst. These findings imply the great potential for the lipase-catalyzed synthesis of N′-alkyl benzohydrazides and extend the utilization of lipase in organic chemistry.

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“…An interesting method to access the benzoxazole ring via oxidative cyclization catalyzed by hemoglobin was recently reported by Wang and co-workers. 46 The use of hemoglobin as a biocatalyst had been reported a few years earlier for the synthesis of (poly)aromatic hydrocarbons. 47 Following this work, hemoglobin from Vitreoscilla (VHb) was selected for its highest catalytic performance after screening different hemoproteins and enabled the synthe-sis of benzoxazoles 124 in excellent yields (up to 94%) from imine precursors 123.…”

Section: Short Review Synthesismentioning

confidence: 99%

Biocatalytic and Chemo-Enzymatic Approaches for the Synthesis of Heterocycles

Zhao¹,

Masci²,

Tomarelli³

et al. 2020

Synthesis

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Heterocycles are ubiquitous structures in nature and can be found in many drugs and chemicals. Biocatalysts, alone or in combination with other metal catalysts, can be exploited for the construction of various heterocyclic rings under mild reaction conditions. This Short Review highlights the recent advances in the development of biocatalytic and chemo-enzymatic methods for the synthesis of both aliphatic and aromatic heterocyclic rings.1 Introduction2 Synthesis of Aliphatic Heterocycles2.1 Piperidines, Pyrrolidines and Piperazines2.2 Other Nitrogen-Containing Aliphatic Heterocycles2.3 Lactones and Lactams2.4 Other Oxygen-Containing Heterocycles3 Synthesis of Aromatic Heterocycles3.1 Pyrroles, Pyridines and Pyrazines3.2 Furans3.3 Bicyclic Aromatic Heterocycles4 Conclusion

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Hemoglobin: A New Biocatalyst for the Synthesis of 2‐substituted Benzoxazoles via Oxidative Cyclization

Abstract: Efficient and mild synthesis of a series of 2‐substituted benzoxazoles via oxidative cyclization catalyzed by hemoglobins reported here for the first time. Satisfactory yields (84 %–97 %) and mild reaction conditions make this method highly viable for practical applications.

Cited by 20 publications

References 41 publications

Hemoglobin‐Catalyzed Synthesis of Indolizines Under Mild Conditions

Hemoglobin‐Catalyzed Synthesis of Indolizines Under Mild Conditions

Lipase‐catalyzed hydrazine insertion for the synthesis of N′‐alkyl benzohydrazides

Biocatalytic and Chemo-Enzymatic Approaches for the Synthesis of Heterocycles

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