Lê Đức Anh * , Bùi Thị Bửu Huê , Nguyễn Quốc Châu Thanh , Phùng Văn Bình Lê Trọng Hiếu

* Tác giả liên hệ (anhm0914001@gstudent.ctu.edu.vn)

Abstract

A one-step synthetic pathway of N-(3-morpholinopropyl)benzimidazole has been developed including in situ reduction/cyclization of N-alkyl-o-nitroanilines and aldehydes using Na2S2O4 as the reducing agent. Based on this method, ten new N-(3-morpholinopropyl)benzimidazole derivatives have been successfully synthesized in moderate to excellent yields (42-91%). The structures of these new compounds were fully confirmed by various spectroscopic methods such as MS, IR, 1H-NMR and 13C-NMR.
Keywords: Benzimidazole, N-alkylbenzimidazole, sodium hydrosulfite

Tóm tắt

Phương pháp một bước đơn giản gồm sự khử/đóng vòng in situ các N-alkyl-o-nitroaniline và các aldehyde tương ứng tạo ra dẫn xuất N-alkylbenzimidazole sử dụng tác nhân oxy hóa là Na2S2O4. Dựa trên phương pháp này, mười dẫn xuất mới N-(3-morpholinopropyl) benzimidazole đã tổng hợp thành công với hiệu suất từ 42-91%. Cấu trúc của các dẫn xuất được xác nhận bằng các phương pháp phổ nghiệm hiện đại như MS, IR, 1H-NMR và 13C-NMR.
Từ khóa: benzimidazole, N-alkylbenzimidazole, sodium hydrosulfite

Article Details

Tài liệu tham khảo

D. Yang, D. Forkas, J. Li, L. Yu and C. M. Baldino, 2005. Benzimidazole derivatives: A Versatile Method for the Synthesis of Benzimidazoles from o-Nitroanilines and Aldehydes in One Step via a Reductive Cyclization. Synthesis, 2005, 47-56.

Geeta Yadav and Swastika Ganguly, 2014. Structure activity relationship (SAR) study of benzimidazole scaffold for different biological activities: A Mini-Review. European Journal of Medicinal Chemistry, 97: 419–443.

Gunaganti Naresh, Ruchir Kant and Tadigoppula Narender, 2014. Molecular Iodine Promoted Divergent Synthesis of Benzimidazoles, Benzothiazoles, and 2Benzyl-3-phenyl-3,4-dihydro2Hbenzo[e][1,2,4]thiadiazines. The Journal of Organic Chemistry, 79: 3821-3829.

Harjyoti Thakuria and Gopal Das, 2008. An expeditious one-pot solvent-free synthesis of benzimidazole derivatives. ARKIVOC, volume 2008, 15, 321-328.

Hue Thi Buu Bui, Quy Thi Kim Ha, Won Keun Oh, Duy Duc Vo, Yen Nguyen Tram Chau, Cuc Thi Kim Tu, Em Canh Pham, Phuong Thao Tran, Loan Thi Tran and Hieu Van Mai, 2015. Microwave Assisted Synthesis and Cytotoxic Activity Evaluations of New Benzimidazole. Tetrahedron Letters, 57 (8): 887–891.

Hue T.B. Bui, Duy D. Vo, Yen N. T. Chau, Cuc T. K. Tu, Hieu V. Mai, Kiet V. Truong, 2015, Facile Synthesis of 4-oxo-4H-quinolizine-2-carboxamide derivatives, Synthetic Communication, 45: 2861–2868.

James R. Gillard and Pierre L. Beaulieu, 2012. Oxone-Mediated Synthesis of Benzimidazoles from 1,2-Phenylenediamines and Aldehydes: Preparation of 2-(4-Cyano-Phenyl)-1-[2-(3,4-Dimethoxyphenyl)-Ethyl]-1H-Benzimidazole-5-Carboxylic Acid Ethyl Ester. Organic Syntheses, 89: 131-142.

Khac Minh Huy Nguyen, 2015. A Bioinspired Catalytic Aerobic Oxidative C-H Functionalization of Primary Aliphatic Amines: Synthesis of 1,2-DisubstitutedBenzimidazoles. ChemPubSoc Europe, 21: 12606 – 12610.

Kiumars Bahrami, Mohammad Mehdi Khodaei and Iman Kavianinia, 2006. A Simple and Efficient One-Pot Synthesis of 2-Substituted Benzimidazoles. Synthesis, 4: 0647-0550.

Mohan Lakshmi Punna Rao Alapatiab, Sridhar Rao Abburiab, Saratchandra Babu Mukkamalaa and M. Krishnaji Rao, 2015. A Simple and Efficient One-Pot Synthesis of 2-Substituted Benzimidazoles from 3-Diaminoarene and Aryl Aldehydes. Synthetic Communication, 45 (21): 2436-2443.

Phạm Cảnh Em, Bùi Thị Bửu Huê, 2015. Tổng hợp dẫn xuất 2-Benzimidazolyl-4-oxo-4H-quinolizine bằng phương pháp hỗ trợ vi sóng. Tạp chí Khoa học Trường Đại học Cần Thơ, 37 (2015): 75-81.

Rui Wang, Xiao-xia Lu, Xiao-qi Yu, Lin Shi and Yong Sun, 2006. Acid-catalyzed solvent-free synthesis of 2-arylbenzimidazoles under microwave irradiation. Journal of Molecular Catalysis, 266: 198–201.

Shinichi Oda, Hideki Shimizu, Yasunori Aoyama, Tatsuo Ueki, Sumio Shimizu, Hiroshi Osato and Yoshiyuki Takeuchi, 2011. Development of Safe One-Pot Synthesis of N-1- and C-2-Substituted Benzimidazole via Reductive Cyclization of o-Nitroarylamine Using Na2S2O4. Organic Process Research & Development, 16: 96–101.

Shweta Sharma, Saloni Gangal and Abdul Rauf, 2008. Convenient one-pot synthesis of novel 2-substituted benzimidazoles, tetrahydrobenzimidazoles and imidazoles and evaluation of their in vitro antibacterial and antifungal activities. European Journal of Medicinal Chemistry, 44: 1751-1757.

Siva S. Panda and Subhash C. Jain, 2011. Synthesis of 2-Arylbenzimidazoles in Water. Synthetic Organic Chemistry, 41: 729-735.

Thanh Binh Nguyen, Ludmila Ermolenko and Ali Al-Mourabit, 2013, Green Chemistry, 15: 2713-2717.

Vishnu K. Tandon and Manoj Kumar, 2004. BF3·Et2O promoted one-pot expeditious and convenient synthesis of 2-substituted benzimidazoles and 3,1,5-benzoxadiazepines. Tetrahedron Letters, 45: 4185–4187.

Xiangming Han, Huiqiang Ma and Yulu Wang, 2007. A Simple and Efficient Synthesis of 2-Aryl-Substituted Benzimidazoles. Russian Journal of Organic Chemistry, 44 (6): 863–865.