Efficient synthesis of unsymmetrical trisubstituted 1,3,5-triazines catalyzed by hemoglobin

Li, Fengxi; Wang, Qianqian; Xu, Yaning; Zhao, Zixian; Su, Jiali; Luo, Chenhan; Ning, Yujie; Li, Zhengqiang; Li, Chen; Wang, Lei

doi:10.1016/j.mcat.2021.111519

Cited by 11 publications

(10 citation statements)

References 39 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Multicomponent reactions (MCRs), an efficient and atom‐economic synthetic strategy to obtain complex compounds in a single step from three or more reactants, are currently gaining considerable importance in chemical synthesis [1–4] . Enzyme catalytic promiscuity, the capability of enzymes to catalyze reactions different from their natural ones, has been a theme in biocatalysis [5–12] . In this area, lipase exhibits broad applications owing to its excellent catalytic promiscuity, stability, and commercial availability.…”

Section: Methodsmentioning

confidence: 99%

“…[1][2][3][4] Enzyme catalytic promiscuity, the capability of enzymes to catalyze reactions different from their natural ones, has been a theme in biocatalysis. [5][6][7][8][9][10][11][12] In this area, lipase exhibits broad applications owing to its excellent catalytic promiscuity, stability, and commercial availability. Many studies have reported the formation of carbon-carbon and carbon-heteroatom bonds, such as Michael addition, perhydrolysis, aldol addition, Morita-Baylis-Hillman reaction, and Knoevenagel condensation.…”

mentioning

confidence: 99%

See 1 more Smart Citation

Lipase‐Catalyzed Synthesis of Anthrone Functionalized Benzylic Amines via a Multicomponent Reaction in Supercritical Carbon Dioxide

Wang

et al. 2022

ChemistrySelect

Self Cite

View full text Add to dashboard Cite

In this study, supercritical carbon dioxide (ScCO2), which is a sustainable and green solvent, was used as a reaction medium in the lipase‐catalyzed synthesis of anthrone‐functionalized benzylic amines for the first time. We synthesized the target compounds via a lipase‐catalyzed multicomponent cascade reaction of aldehydes, sulfonamides, and anthrones in ScCO2. The reaction can be accomplished in good‐to‐excellent yields (77 %–95 %) and can exhibit good functional group tolerance. In brief, the reaction was characterized by step economy, metal‐free conditions, environmentally friendly solvents, and biocatalysts.

show abstract

Section: Methodsmentioning

confidence: 99%

mentioning

confidence: 99%

Lipase‐Catalyzed Synthesis of Anthrone Functionalized Benzylic Amines via a Multicomponent Reaction in Supercritical Carbon Dioxide

Wang

et al. 2022

ChemistrySelect

Self Cite

View full text Add to dashboard Cite

show abstract

“…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 . 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: Introductionmentioning

confidence: 99%

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

et al. 2022

Biotech and App Biochem

Self Cite

View full text Add to dashboard Cite

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.

show abstract

“…As guanidine groups are highly basic (pK a = 12.3), these have found many applications as a catalyst in organic synthesis. [41][42][43][44] In this context, TMG has demonstrated to trigger the esterification reaction of carboxylic acids with alkyl halides under room temperature conditions. 42,45 This efficient reaction has recently been exploited to prepare both monomers and polymers based on sustainable renewable resources.…”

mentioning

confidence: 99%

“…[41][42][43][44] In this context, TMG has demonstrated to trigger the esterification reaction of carboxylic acids with alkyl halides under room temperature conditions. 42,45 This efficient reaction has recently been exploited to prepare both monomers and polymers based on sustainable renewable resources. [45][46][47] Herein, we made use of this reaction with the final aim of providing multifunctional precursors, that is, di-, tri-, and tetrabenzoxazines based on phloretic acid (Scheme 2).…”

mentioning

confidence: 99%

Tetramethyl guanidine‐assisted synthesis and thermal crosslinking of multifunctional benzoxazine monomers based on natural phloretic acid

Casarino

Moreno

Galià

et al. 2021

Journal of Polymer Science

View full text Add to dashboard Cite

An efficient strategy to synthesize novel biobased multifunctional benzoxazine compounds was developed using the 1,1,3,3-tetramethyl guanidine (TMG)triggered esterification of natural phloretic acid with organic halides as a key synthetic step. First, phloretic acid was combined with either aniline or furfurylamine to prepare the corresponding carboxylic acid-functional monobenzoxazine monomer. Next, the use of TMG enabled an efficient esterification of these compounds with di-, tri-, and tetra-functional benzyl bromide compounds at room temperature to afford a series of new multi-benzoxazine monomers tethered to an aromatic core. The effect of the functionality of the monomers on the curing process was analyzed, indicating that the reactivity during the thermally induced ring-opening increases with the number of furan and oxazine rings in the monomers. The resulting thermosets revealed good correlation between the number of oxazine rings in the structure of the monomer and the properties of the crosslinked materials. Furfurylamine-based polybenzoxazines showed improved thermal behavior compared to the anilinebased systems, due to the role of furan rings. All materials showed high T g , good thermal stability, and promising flame retardancy properties.

show abstract

Efficient synthesis of unsymmetrical trisubstituted 1,3,5-triazines catalyzed by hemoglobin

Cited by 11 publications

References 39 publications

Lipase‐Catalyzed Synthesis of Anthrone Functionalized Benzylic Amines via a Multicomponent Reaction in Supercritical Carbon Dioxide

Lipase‐Catalyzed Synthesis of Anthrone Functionalized Benzylic Amines via a Multicomponent Reaction in Supercritical Carbon Dioxide

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

Tetramethyl guanidine‐assisted synthesis and thermal crosslinking of multifunctional benzoxazine monomers based on natural phloretic acid

Contact Info

Product

Resources

About