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

被引:20
作者
Li, Fengxi [1 ]
Wang, Chunyu [3 ]
Xu, Yaning [1 ]
Zhao, Zixian [1 ]
Su, Jiali [1 ]
Luo, Chenhan [1 ]
Ning, Yujie [1 ]
Li, Zhengqiang [1 ]
Li, Chen [2 ]
Wang, Lei [1 ]
机构
[1] Jilin Univ, Sch Life Sci, Minist Educ, Key Lab Mol Enzymol & Engn, Changchun 130023, Peoples R China
[2] Jilin Univ, Coll Vet Med, Inst Zoonosis, Key Lab Zoonosis Res,Minist Educ, Changchun 130062, Peoples R China
[3] Jilin Univ, State Key Lab Supramol Struct & Mat, Changchun 130023, Peoples R China
来源
MOLECULAR CATALYSIS | 2021年 / 505卷
基金
中国国家自然科学基金;
关键词
Hemoglobin; Biocatalysis; Synthetic methods; Unsymmetrical 1,3,5-triazines; Oxidative cyclization;
D O I
10.1016/j.mcat.2021.111519
中图分类号
O64 [物理化学(理论化学)、化学物理学];
学科分类号
070304 ; 081704 ;
摘要
Background: 1,3,5-triazines are important bioactive compounds that have been extensively studied in organic chemistry. In this work, a green and efficient process for the synthesis of unsymmetrical trisubstituted 1,3,5-triazines from isothiocyanate (1) with amidines (2) and 1,1,3,3-tetramethylguanidine (TMG, 3) was developed. Results: Under optimal conditions (isothiocyanate (0.1 mmol), amidines (0.1 mmol), 1,1,3,3-tetramethylguanidine (0.1 mmol), HMSO (1 mL), hemepmtein (heme concentration: 0.05 mol%), TBHP (3 equiv), room temperature, 10 min), high yields of 1,3,5-triazines (81%-96%) could be obtained when HbRb (Hemoglobin from rabbit blood) was used as the catalyst. Conclusion: This enzymatic method demonstrates the great potential for the synthesis of unsymmetrical trisubstituted 1,3,5-triazines and extends the application of enzyme catalytic promiscuity in organic synthesis.
引用
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页数:7
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