(3+2) Annulation of amidinothioureas with binucleophile: Synthesis and antimicrobial of 3-phenylamino-5-aryl/alkyl-1,2,4-oxadiazole derivatives
作者： Swapnil G. Yerande , Amruta B. Ghaisas , Kiran M. Newase , Wei Wang , Kan Wang
DOI: 10.1002/JHET.1873
关键词:
摘要: Herein, we report an efficient method for preparation of 3-phenylamino-5-aryl/alkyl-1,2,4-oxadiazole by (3+2) annulation amidinothioureas with binucleophilic hydroxylamine hydrochloride in the presence mercury (II) chloride. Desired was prepared good to moderate yields. On basis literature precedence, mechanism formation is proposed. The synthesized compounds were tested their antimicrobial activity and showed promising inhibition Gram-positive bacteria (Staphylococcus aureus) fungi (Candida albicans).
narcis.nl参考文章(29)
V. N. Yarovenko, V. Z. Shirinyan, I. V. Zavarzin, M. M. Krayushkin, A convenient synthesis of 3-substituted 5-guanidino-1,2,4-oxadiazoles Russian Chemical Bulletin. ,vol. 43, pp. 114- 117 ,(1994) , 10.1007/BF00699147
Michael A. Poss, Edwin Iwanowicz, Joyce A. Reid, James Lin, Zhengxiang Gu, A mild and efficient method for the preparation of guanidines Tetrahedron Letters. ,vol. 33, pp. 5933- 5936 ,(1992) , 10.1016/S0040-4039(00)61092-4
I. M. Coupar, Annmarie Hedges, Helen L. Metcalfe, P. Turner, Effect of aminophylline, butalamine and imolamine on human isolated smooth muscle. Journal of Pharmacy and Pharmacology. ,vol. 21, pp. 474- 475 ,(2011) , 10.1111/J.2042-7158.1969.TB08294.X
J.W. Clitherow, P. Beswick, W.J. Irving, D.I.C. Scopes, J.C. Barnes, J. Clapham, J.D. Brown, D.J. Evans, A.G. Hayes, Novel 1, 2, 4-oxadiazoles as potent and selective histamine H3 receptor antagonists Bioorganic & Medicinal Chemistry Letters. ,vol. 6, pp. 833- 838 ,(1996) , 10.1016/0960-894X(96)00122-9
Han-Zhong Zhang, Shailaja Kasibhatla, Jared Kuemmerle, William Kemnitzer, Kristin Ollis-Mason, Ling Qiu, Candace Crogan-Grundy, Ben Tseng, John Drewe, Sui Xiong Cai, Discovery and Structure−Activity Relationship of 3-Aryl-5-aryl-1,2,4-oxadiazoles as a New Series of Apoptosis Inducers and Potential Anticancer Agents Journal of Medicinal Chemistry. ,vol. 48, pp. 5215- 5223 ,(2005) , 10.1021/JM050292K
Kyoung Soon Kim, Ligang Qian, Improved method for the preparation of guanidines Tetrahedron Letters. ,vol. 34, pp. 7677- 7680 ,(1993) , 10.1016/S0040-4039(00)61537-X
William Kemnitzer, Jared Kuemmerle, Han-Zhong Zhang, Shailaja Kasibhatla, Ben Tseng, John Drewe, Sui Xiong Cai, Discovery of 3-aryl-5-aryl-1,2,4-oxadiazoles as a new series of apoptosis inducers. 2. Identification of more aqueous soluble analogs as potential anticancer agents. Bioorganic & Medicinal Chemistry Letters. ,vol. 19, pp. 4410- 4415 ,(2009) , 10.1016/J.BMCL.2009.05.052
Dalip Kumar, Gautam Patel, Emmanuel O. Johnson, Kavita Shah, Synthesis and anticancer activities of novel 3,5-disubstituted-1,2,4-oxadiazoles Bioorganic & Medicinal Chemistry Letters. ,vol. 19, pp. 2739- 2741 ,(2009) , 10.1016/J.BMCL.2009.03.158
Kurt Wermann, Martin Walther, Wolfgang Günther, Helmar Görls, Ernst Anders, Novel triazinium-imidothioate zwitterions: intermediates in the reaction of [1,3,4]thiadiazolo[2,3-d][1,2,4]triazolo[1,5-a][1,3,5]triazinium cations with amines Tetrahedron. ,vol. 61, pp. 673- 685 ,(2005) , 10.1016/J.TET.2004.10.081
Gundala Chennakrishnareddy, Hazra Debasis, Rapai Jayan, Sulur G. Manjunatha, Facile synthesis of 3-aryl/alkylamino 5-aryl/alkyl 1,2,4-oxadiazoles from acylthiourea Tetrahedron Letters. ,vol. 52, pp. 6170- 6173 ,(2011) , 10.1016/J.TETLET.2011.09.048