Letter Cite This: ACS Sustainable Chem. Eng. XXXX, XXX, XXX−XXX
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Highly Atom-Economic, Catalyst-Free, and Solvent-Free Synthesis of Phthalazinones Bowei Lu,†,‡,∥ Zhiqiang Xie,§,∥ Junrui Lu,*,† Jinbiao Liu,† Siqian Cui,†,‡ Yao Ma,† Xinlong Hu,† Yue Liu,† and Kaikai Zhong†
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†
College of Chemistry and Chemical Engineering, Tianjin University of Technology, No. 391, Binshui West Road, Xiqing District, Tianjin 300384, P. R. China ‡ School of Chemical Engineering and Technology, Tianjin University, No. 135, Yaguan Road, Haihe Education Park, Jinnan District, Tianjin 300072, P. R. China § Tianjin Ruiling Chemical Co., Ltd., No. 1,Gonghua Road, Huayuan Hi-tech Park, Tianjin 300384, P. R. China S Supporting Information *
ABSTRACT: Herein a simple, catalyst- and solvent-free system for highly atom-economic synthesis of phthalazinones has been developed using phthalaldehydic acid, 2-acyl-benzoic acid, and substituted hydrazine as simple substrates. The reaction time was shortened to 20−60 min. Structurally diverse phthalaldehydic acids, 2-acyl-benzoic acids, and hydrazines were transformed into phthalazinones with a nearly 100% yield regardless of the aggregate state and electronic nature of the substituents. The transformation was demonstrated to be amenable for scale-up with multiple liquid and solid materials. In addition, isolation and purification of the crude products can be simply done with only crystallization. The heavy metal pollution was also eliminated from the source. KEYWORDS: Highly atom economic, Catalyst free, Solvent free, Phthalazinones, Green synthesis
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INTRODUCTION With the growing awareness of sustainable development, the international chemical community is under increasing pressure to change current inefficient and pollutional working practices and find greener alternatives represented by reductions in cost, waste, energy use, material consumption, risk, hazards, and usage amounts of nonrenewable resources. Therefore, green chemistry has attracted worldwide attention by more and more research groups because of its environmentally benign transformation.1−9 Atom economy is one of the fundamental principles of green chemistry. Maximizing the efficiency of reactants and minimizing the production of waste are essential contributions to high atom economy and green chemistry. Much research has been initiated in the development of new chemical transformations. Among them, the replacement or even avoidance of hazardous solvents and catalysts in chemical processes has required urgent attention in academia and industry. This research direction is beneficial to waste reduction, enhanced cost efficiency, operational simplicity, environmental protection, and people’s health. Furthermore, reactions of neat reactants without metal catalysts can eliminate lethal heavy metal pollution from the source and enhance the purity of products, which is a desired solution for synthesis of active pharmaceutical ingredients (APIs) and biologicals. However, many reactions still suffer from low atom economy because of incomplete transformation or byproducts generated simultaneously with the desired product. New strategies to improve the atom economy of significant chemical processes and valuable structures are still in great demand. © XXXX American Chemical Society
Nitrogen-containing heterocycles are core segments in a broad range of active compounds found frequently in pharmaceutical drugs, agrochemicals, and functional materials.10−22 Among these, phthalazinones are a group of condensed heterocycles having significant biological activities which show great potential in the treatment of various pathological processes including diabetes,23,24 hepatitis B,25 vascular hypertension,26,27 asthma,28,29 and arrhythmia.30 Azelastine is a well-known antiallergic and antihistaminic drug with $0.24 billion in sales in 200829,31 as a phthalazinone derivative. The phthalazinone moiety acts importantly as the key building block in some agents related to cancer therapy and anti-inflammatory response typically, such as a vascular endothelial growth factor (VEGF) inhibitor,32 poly(ADPribose) polymerase-1 (PARP-1) inhibitor,33 and liphosphodiesterase-4 (PDE-4) inhibitor.34 Moreover, phthalazinone derivatives have been attracting considerable attention in the development of novel antiasthmatic agents with dual activities of thromboxane A2 (TXA2) synthetase inhibition and bronchodilation.35 (Figure 1). Because of the significant value in pharmaceuticals, the synthetic research of phthalazinones represents a continuing interest.36−39 In general, two categories of reactions have been developed to assemble phthalazinones. Traditional methods are based on the two-component [4 + 2] cyclocondensation of Received: November 2, 2018 Revised: December 4, 2018 Published: December 10, 2018 A
DOI: 10.1021/acssuschemeng.8b05657 ACS Sustainable Chem. Eng. XXXX, XXX, XXX−XXX
Letter
ACS Sustainable Chemistry & Engineering
component [4 + 2] procedure with nearly 100% yields, short reaction time, and benign temperature to prepare various analytical grade substituted phthalazinones from phthalaldehydic acid, 2-acyl-benzoic acid, and substituted hydrazine without solvents or catalysts (Scheme 1c), aiming to realize green chemistry. This environmentally benign reaction system also eliminates heavy metal pollution and increases atomic economy.
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RESULTS AND DISCUSSION The reaction temperature is crucial for this solvent-free system to directly influence the molten condition, mixing uniformity, and reaction rate. Considering the melting points and uniformity of reactants and the activation energy of cyclocondensation, the reaction temperature was set from 70 to 130 °C to obtain positively related yields without any byproducts (Table 1). Above 90 °C, the yield was nearly 100%. The Table 1. Optimization of Reaction Conditionsa Figure 1. Examples of biologically active phthalazinones.
2-carboxybenzaldehydes and substituted hydrazine with catalysts like nano TiO2,40 palladium,41 Pt nanowires,42 heteropolyacids,43 HClO4−SiO2,44 and solid acid45 (Scheme 1a). Recent researches tended to use the three-component [3 Scheme 1. Various Procedures for Synthesis of Phthalazinones
Entry
t (min)
T (°C)
Status
Yield (%)b
1 2 3 4 5 6 7 8
very long 30 30 30 30 30 30 30
60 70 80 90 100 110 120 130
half molten half molten molten molten molten molten molten molten
very low 85.23 95.78 98.76 99.25 99.22 99.31 99.26
a
Conditions: 1a (20 mmol), 2 (20 mmol), no catalyst, solvent-free, 30 min. bIsolated yield.
reaction rate below 70 °C was extremely slow even though several days passed. This method under mild temperature was also indicated to possess exclusive chemoselectivity and outstanding atomic economy since the impurities existing after reactions were only unreacted substrates, which can be easily separated and recycled. To study the effect of solvent on reaction yield, a range of solvents such as acetonitrile, ethyl acetate, THF, toluene, trichloromethane, and dioxane were examined (Table 2). Compared with a solvent-based reaction system, solvent-free conditions lead to not only higher yield but also shorter reaction time obviously. It means that the key point in this Table 2. Effects of Solvents + 2+1] cyclocondensation of 2-brominated benzoic acid derivatives or 2-bromo-benzoic acid methyl ester derivatives, arylhydrazines, and a carbonyl source generally under the palladium-catalysis conditions (Scheme 1b).41,46−49 In fact, neither of these methods could reduce the actual usage of organic solvent and expensive additives, shorten the reaction time, optimize the reaction conditions (strong acid and base, high temperature), simplify the postprocessing, or improve the yields. Even worse, the toxic metal residues coming from the catalysts were difficult to be removed thoroughly in target phthalazinones. Herein, we report a simple and efficient two-
Entry
Solvent
T (°C)
t (h)
1 2 3 4 5 6 7
solvent-free toluene dioxane ethyl acetate acetonitrile thf trichloromethane
100 reflux reflux reflux reflux reflux reflux
0.5 8 8 8 8 8 8
Yield (%)a
,b
99.25 52.64 42.76 40.75 35.36 23.89 23.26
a Conditions: 1a (20 mmol, 2 mmol/mL), 2a (20 mmol, 2 mmol/ mL), no catalyst. bIsolated yield.
B
DOI: 10.1021/acssuschemeng.8b05657 ACS Sustainable Chem. Eng. XXXX, XXX, XXX−XXX
Letter
ACS Sustainable Chemistry & Engineering Table 3. Reactions between Substituted Phthalaldehydic Acid, 2-Acyl-Benzoic Acid, and Substituted Hydrazines
t (min)
Product
Yield (%)c
Purity (%)
H H H H H H H
30 30 30 20 20 30 60
3a 3b 3c 3d 3e 3f 3g
98.95 98.36 99.21 98.14 96.14 99.62 98.48
H
H
60
3h
p-ClC6H4
H
H
60
3i
10
p-FC6H4
H
H
60
3j
11
p-NO2C6H4
H
H
60
3k
12 13 14 15 16 17 18
p-MeC6H4 pyridine Ph Ph Ph Ph Ph
H H 3,4-di-OMe H H H H
H H H CH3 Ph p-MeC6H4 p-ClC6H4
60 60 60 30 30 30 30
3l 3m 3n 3o 3p 3q 3r
99.25a,c 99.66a,c 99.38a,c 98.67a,c 97.52a,c 99.47a,c 98.44b,d 87.94b,c 98.63b,d 90.47b,c 98.24b,d 93.77b,c 97.92b,d 93.15b,c 98.13b,d 86.01b,c 97.88a,c 97.53a,c 98.23a,c 99.15a,c 98.49a,c 98.40a,c 98.04a,c
Entry
R
R1
1 2 3 4 5 6 7
Ph H CH3 i-Pr t-Bu CH2CH2OH o-ClC6H4
H H H H H H H
8
m-ClC6H4
9
R2
96.26 99.13 99.03 92.46 99.62 99.08 99.56 99.02 98.82 97.24 97.62
Conditions: 1 (20 mmol), 2 (20 mmol), no catalyst and solvent-free, 100 °C. bConditions: 1 (20 mmol), 2 (20 mmol), no catalyst and solventfree, 150 °C. cIsolated yield. dYield based on recovered starting materials.
a
reaction process is the concentration of reactants rather than solvent effect. Under high concentration of reactants, the aldehyde group of 2a can be attacked by the primary amino group of 1a easily without catalysts. Consequently, the solventfree melting reaction in equimolar ratio without catalysts was therefore chosen as the optimum condition to further expand different reactants. With the optimal conditions defined, a variety of substituted phthalaldehydic acid, 2-acyl-benzoic acid, and substituted hydrazines were selected to expand the scope of this [4 + 2] cyclocondensation reaction (Table 3). The reaction temperature for 3a−3f and 3l−3r was 100 °C and for 3g−3k was 150 °C to achieve the optimum yields. All the reactions have proceeded efficiently and resulted in nearly 100% yield without any byproducts regardless of the aggregate state and electronic nature of the substituents. This simple and convenient experimental procedure tolerates a variety of functional groups such as hydroxyethyl (Table 3, entry 6), bulky groups (Table 3, entries 4 and 5), substituted phenyl (Table 3, entries 7−12), and even heterocyclic (Table 3, entry 13) groups with desired yields and can be applied among “liquid−liquid” and “liquid-solid” conditions, which usually occur faster than performed in solution. A variety of 2-acyl-benzoic acids were selected as reactants (Table 3, entries 15−18). The reaction process was smooth as well and provided the corresponding phthalazinone derivatives 3o−3r in excellent yields (98%−100%). This method would be likely to synthesize complex biological active phthalazinones with multiple substituents, such as azelastine.
Our results indicate that the synthesis of phthalazinones in this method proceeds quickly with nearly 100% overall yields without byproducts. Because of exclusive chemoselectivity, the purity of most products was over 99% only through primary crystallization (Table 3). Distinguished from the traditional synthetic method, this catalyst-free condition can eliminate heavy metal pollution from the source. The target compounds were analyzed by ICPMS to detect traces of metallic elements. The results proved that there was no metal residue detected in the products by this method. This work will apply to the synthesis of active pharmaceutical ingredients (APIs) and biologicals.
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CONCLUSIONS
In summary, our catalyst-free and solvent-free method was successful for the synthesis of a broad variety of biologically interesting functionalized phthalazinone derivatives with nearly 100% yields and over 99% purity in a short reaction time. This new method possesses great atomic economy without byproducts and avoids heavy metal pollution from the source. Based on these findings, a simple, efficient, and environmentally friendly method has been developed from readily available and cheap reagents. Further research is underway in our laboratory. C
DOI: 10.1021/acssuschemeng.8b05657 ACS Sustainable Chem. Eng. XXXX, XXX, XXX−XXX
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ACS Sustainable Chemistry & Engineering
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ASSOCIATED CONTENT
* Supporting Information S
The Supporting Information is available free of charge on the ACS Publications website at DOI: 10.1021/acssuschemeng.8b05657. Experimental section and characterization data of the products. (PDF)
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AUTHOR INFORMATION
Corresponding Author
*E-mail:
[email protected]. ORCID
Junrui Lu: 0000-0002-9647-8986 Author Contributions ∥
Bowei Lu and Zhiqiang Xie contributed equally.
Notes
The authors declare no competing financial interest.
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ACKNOWLEDGMENTS We gratefully acknowledge the financial support from the National Natural Science Foundation of China (No. 21476174; No. 21176194).
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DOI: 10.1021/acssuschemeng.8b05657 ACS Sustainable Chem. Eng. XXXX, XXX, XXX−XXX
