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Silver-catalyzed tandem hydroamination/hydroarylation of 1-(2-allylamino)phenyl-4-hydroxy-but-2-yn-1-ones to 1'-allylspiro[indene-1,2'-indolin]-3'-ones.
Org Lett. 2014 Aug 15; 16(16):4110-3.OL

Abstract

An efficient silver triflate-catalyzed tandem hydroamination/hydroarylation cascade generating 1'-allylspiro[indene-1,2'-indolin]-3'-ones from 1-(2-allylamino)phenyl-4-hydroxy-but-2-yn-1-ones is described. The reaction conditions are mild and general in scope and proceed to highly functionalized spiro-targets in high yield. This novel class of molecule possesses both the privileged indene and indolin-3-one scaffold, which may lead to possible pharmacological applications.

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Publisher Full Text (DOI)

Authors+Show Affiliations

Mothe SR
Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University , Singapore 637371, Singapore.
Novianti ML
No affiliation info available
Ayers BJ
No affiliation info available
Chan PW
No affiliation info available

MeSH

CatalysisCyclizationIndenesIndolesMesylatesMolecular StructureSilverSpiro Compounds

Pub Type(s)

Journal Article
Research Support, Non-U.S. Gov't

Language

eng

PubMed ID

25076131

Citation

Mothe, Srinivasa Reddy, et al. "Silver-catalyzed Tandem Hydroamination/hydroarylation of 1-(2-allylamino)phenyl-4-hydroxy-but-2-yn-1-ones to 1'-allylspiro[indene-1,2'-indolin]-3'-ones." Organic Letters, vol. 16, no. 16, 2014, pp. 4110-3.
Mothe SR, Novianti ML, Ayers BJ, et al. Silver-catalyzed tandem hydroamination/hydroarylation of 1-(2-allylamino)phenyl-4-hydroxy-but-2-yn-1-ones to 1'-allylspiro[indene-1,2'-indolin]-3'-ones. Org Lett. 2014;16(16):4110-3.
Mothe, S. R., Novianti, M. L., Ayers, B. J., & Chan, P. W. (2014). Silver-catalyzed tandem hydroamination/hydroarylation of 1-(2-allylamino)phenyl-4-hydroxy-but-2-yn-1-ones to 1'-allylspiro[indene-1,2'-indolin]-3'-ones. Organic Letters, 16(16), 4110-3. https://doi.org/10.1021/ol501809p
Mothe SR, et al. Silver-catalyzed Tandem Hydroamination/hydroarylation of 1-(2-allylamino)phenyl-4-hydroxy-but-2-yn-1-ones to 1'-allylspiro[indene-1,2'-indolin]-3'-ones. Org Lett. 2014 Aug 15;16(16):4110-3. PubMed PMID: 25076131.
* Article titles in AMA citation format should be in sentence-case
TY - JOUR T1 - Silver-catalyzed tandem hydroamination/hydroarylation of 1-(2-allylamino)phenyl-4-hydroxy-but-2-yn-1-ones to 1'-allylspiro[indene-1,2'-indolin]-3'-ones. AU - Mothe,Srinivasa Reddy, AU - Novianti,Maria Laurentia, AU - Ayers,Benjamin James, AU - Chan,Philip Wai Hong, Y1 - 2014/07/30/ PY - 2014/7/31/entrez PY - 2014/7/31/pubmed PY - 2015/5/23/medline SP - 4110 EP - 3 JF - Organic letters JO - Org Lett VL - 16 IS - 16 N2 - An efficient silver triflate-catalyzed tandem hydroamination/hydroarylation cascade generating 1'-allylspiro[indene-1,2'-indolin]-3'-ones from 1-(2-allylamino)phenyl-4-hydroxy-but-2-yn-1-ones is described. The reaction conditions are mild and general in scope and proceed to highly functionalized spiro-targets in high yield. This novel class of molecule possesses both the privileged indene and indolin-3-one scaffold, which may lead to possible pharmacological applications. SN - 1523-7052 UR - https://www.unboundmedicine.com/medline/citation/25076131/Silver_catalyzed_tandem_hydroamination/hydroarylation_of_1__2_allylamino_phenyl_4_hydroxy_but_2_yn_1_ones_to_1'_allylspiro[indene_12'_indolin]_3'_ones_ DB - PRIME DP - Unbound Medicine ER -