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σ2P,O-hybrid ligands: Synthesis of the first 4-hydroxy-1,3-benzazaphospholes by ortho-lithiation of M-amidophenyl diethyl phosphates

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dc.contributor.author Aluri B.
dc.contributor.author Shah K.
dc.contributor.author Gupta N.
dc.contributor.author Fomina O.
dc.contributor.author Yakhvarov D.
dc.contributor.author Ghalib M.
dc.contributor.author Jones P.
dc.contributor.author Schulzke C.
dc.contributor.author Heinicke J.
dc.date.accessioned 2018-09-18T20:22:30Z
dc.date.available 2018-09-18T20:22:30Z
dc.date.issued 2014
dc.identifier.issn 1434-1948
dc.identifier.uri https://dspace.kpfu.ru/xmlui/handle/net/139221
dc.description.abstract Copyright © 2014 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim. 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.
dc.relation.ispartofseries European Journal of Inorganic Chemistry
dc.subject Amides
dc.subject Lithiation
dc.subject Phosphorus heterocycles
dc.subject Phosphorylation
dc.subject Rearrangement
dc.title σ2P,O-hybrid ligands: Synthesis of the first 4-hydroxy-1,3-benzazaphospholes by ortho-lithiation of M-amidophenyl diethyl phosphates
dc.type Article
dc.relation.ispartofseries-issue 34
dc.relation.ispartofseries-volume 2014
dc.collection Публикации сотрудников КФУ
dc.relation.startpage 5958
dc.source.id SCOPUS14341948-2014-2014-34-SID84913554867


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  • Публикации сотрудников КФУ Scopus [24551]
    Коллекция содержит публикации сотрудников Казанского федерального (до 2010 года Казанского государственного) университета, проиндексированные в БД Scopus, начиная с 1970г.

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