1312305-91-1Relevant articles and documents
σ2P,O-hybrid ligands: Synthesis of the first 4-hydroxy-1,3-benzazaphospholes by ortho-lithiation of M-amidophenyl diethyl phosphates
Aluri, Bhaskar R.,Shah, Kirti,Gupta, Neelima,Fomina, Olga S.,Yakhvarov, Dmitry G.,Ghalib, Mohammed,Jones, Peter G.,Schulzke, Carola,Heinicke, Joachim W.
, p. 5958 - 5968 (2014)
The m-phosphorylanilides 2 are available from anilides 1 by the Atherton-Todd reaction; the selective ortho-lithiation of the o'-methyl-protected phosphorylpivalanilide 2b with tBuLi proceeded in high yield in the presence of ClSiMe3. The ortho-lithiation is followed by rapid 1,3-migration of the PO3Et2 group to yield the phosphonoanilide cis/trans-3b. This compound mainly reacts with excess LiAlH4 by reductive cyclization to form the 4-hydroxy-1H-1,3-benzazaphosphole 6. The lithiation of the o'-unprotected phosphorylpivalanilide 2a with LDA was unselective and led to 3a and 4a in low yields, whereas additional ortho-lithiation of the benzoyl group occurred for the lithiation of the o'-protected phosphonobenzanilide 2c with tBuLi/LDA to give 7 in rather low yield. The reduction of crude 7 led to (benzylamino)phenol 8 and the 4-hydroxy-1H-1,3-benzazaphosphole 9 as a minor product. The properties, NMR spectroscopy data, and crystal structures of 5b, 6, and 8 are reported.
Design, synthesis and antiviral activity of novel quinazolinones
Wang, Ziwen,Wang, Mingxiao,Yao, Xue,Li, Yue,Tan, Juan,Wang, Lizhong,Qiao, Wentao,Geng, Yunqi,Liu, Yuxiu,Wang, Qingmin
experimental part, p. 275 - 282 (2012/08/07)
HIV-1 integrase (IN) is a validated therapeutic target for antiviral drug design. However, the emergence of viral strains resistant to clinically studied IN inhibitors demands the discovery of novel inhibitors that are structurally as well as mechanistica