Eco-Friendly Syntheses of 2-Substituted Benzoxazoles and 2-Substituted Benzothiazoles from 2-Aminophenols, 2-Aminothiophenols and DMF Derivatives in the Presence of Imidazolium Chloride
作者： Qingqiang Tian , Wen Luo , Zongjie Gan , Dan Li , Zeshu Dai
DOI: 10.3390/MOLECULES24010174
关键词:
摘要: A simple, economical and metal-free approach to the synthesis of 2-substituted benzoxazoles benzothiazoles from 2-aminophenols, 2-aminothiophenols DMF derivatives, only using imidazolium chloride (50% mmol) as promoter without any other additive, was reported. Various were thus prepared in moderate excellent yields.
mdpi.com
doaj.org参考文章(47)
Mahesuni Srinivas, Abhinandan D. Hudwekar, Vunnam Venkateswarlu, G. Lakshma Reddy, K.A. Aravinda Kumar, Ram A. Vishwakarma, Sanghapal D. Sawant, A metal-free approach for transamidation of amides with amines in aqueous media Tetrahedron Letters. ,vol. 56, pp. 4775- 4779 ,(2015) , 10.1016/J.TETLET.2015.06.052
Russell D. Viirre, Ghotas Evindar, Robert A. Batey, Copper-Catalyzed Domino Annulation Approaches to the Synthesis of Benzoxazoles under Microwave-Accelerated and Conventional Thermal Conditions Journal of Organic Chemistry. ,vol. 73, pp. 3452- 3459 ,(2008) , 10.1021/JO702145D
Zafer Asim Kaplancikli, Gülhan Turan-Zitouni, Gilbert Revial, Kiymet Guven, Synthesis and study of antibacterial and antifungal activities of novel 2-[[(benzoxazole/benzimidazole-2-yl)sulfanyl] acetylamino]thiazoles. Archives of Pharmacal Research. ,vol. 27, pp. 1081- 1085 ,(2004) , 10.1007/BF02975108
Banavara L. Mylari, Thomas A. Beyer, Pamela J. Scott, Charles E. Aldinger, Michael F. Dee, Todd W. Siegel, William J. Zembrowski, Potent, orally active aldose reductase inhibitors related to zopolrestat: surrogates for benzothiazole side chain. Journal of Medicinal Chemistry. ,vol. 35, pp. 457- 465 ,(1992) , 10.1021/JM00081A006
Stefania Aiello, Geoffrey Wells, Erica L Stone, Hachemi Kadri, Rana Bazzi, David R Bell, Malcolm FG Stevens, Charles S Matthews, Tracey D Bradshaw, Andrew D Westwell, None, Synthesis and biological properties of benzothiazole, benzoxazole, and chromen-4-one analogues of the potent antitumor agent 2-(3,4-dimethoxyphenyl)-5-fluorobenzothiazole (PMX 610, NSC 721648). Journal of Medicinal Chemistry. ,vol. 51, pp. 5135- 5139 ,(2008) , 10.1021/JM800418Z
Jacques Muzart, N,N-Dimethylformamide: much more than a solvent Tetrahedron. ,vol. 65, pp. 8313- 8323 ,(2009) , 10.1016/J.TET.2009.06.091
Valentin N. Bochatay, Patrick J. Boissarie, John A. Murphy, Colin J. Suckling, Stuart Lang, Mechanistic exploration of the palladium-catalysed process for the synthesis of benzoxazoles and benzothiazoles Journal of Organic Chemistry. ,vol. 78, pp. 1471- 1477 ,(2013) , 10.1021/JO302544D
Xian Huang, Jing Tang, Solid phase synthesis of benzothiazole and thiophene derivatives based on resin-bound cyclic malonic acid ester Tetrahedron. ,vol. 59, pp. 4851- 4856 ,(2003) , 10.1016/S0040-4020(03)00688-4
Ian Hutchinson, Sharon A. Jennings, B. Rao Vishnuvajjala, Andrew D. Westwell, Malcolm F. G. Stevens, Antitumor Benzothiazoles. 16.1 Synthesis and Pharmaceutical Properties of Antitumor 2-(4-Aminophenyl)benzothiazole Amino Acid Prodrugs Journal of Medicinal Chemistry. ,vol. 45, pp. 744- 747 ,(2002) , 10.1021/JM011025R
Sadananda Ranjit, Xiaogang Liu, Direct Arylation of Benzothiazoles and Benzoxazoles with Aryl Boronic Acids Chemistry - A European Journal. ,vol. 17, pp. 1105- 1108 ,(2011) , 10.1002/CHEM.201002787