Michael/hemiketalization of 2-hydroxy-1,4-naphthoquinone to oxindole ketoester was studied using a series of chiral bifunctional organocatalysts. Good yields (up to 91%) and excellent enantioselectivities (up to 98%) were achieved by using a proline derived thiourea catalyst. This method provides an elegant synthetic route to access oxindole containing naphthoquinone derivatives. © 2016 The Royal Society of Chemistry.

Venkitasamy Kesavan

Department Of Biotechnology

V. Pratap Reddy Gajulapalli

Kanduru Lokesh

Manjunatha Vishwanath

CATALYSTS

Thioureas

2-HYDROXY-1 ,4-NAPHTHOQUINONE

Bi-functional

Naphthoquinone

Naphthoquinones

Organocatalysts

Organocatalytic

Synthetic routes

THIOUREA CATALYSTS

Ketones

Fulltext

IIT Madras is a public technical and research university located in Chennai, Tamil Nadu. Founded in 1959, it is recognised as an Institute of National Importance.

IIT Madras has been ranked as the top engineering institute in India for four years in a row by the National Institutional Ranking Framework of the MHRD

It currently offers undergraduate, postgraduate and research degrees across 16 disciplines in Engineering, Sciences, Humanities and Management. About 596 faculty belonging to science and engineering departments and centres of the Institute are engaged in teaching, research and industrial consultancy.

IIT Madras

RSC Advances

3-Alkynyl-3-OBoc oxindoles underwent Cu(II) mediated Friedel-Crafts alkylation with indoles and phenols to yield of structurally diverse 3-alkynyl-3-indole/phenol-oxindole derivatives. The synthetic application of alkylated phenol derivatives were further demonstrated to biologically important new class of chromene fused spirooxindoles through intramolecular metal-free iodocyclization under mild reaction conditions with broad substrate scope in very good yields. © 2018 Elsevier Ltd

Tetrahedron Letters

Efficient synthesis of highly functionalized indole and phenol containing 3,3′-disubstituted oxindoles and chromene fused spirooxindoles

Organocatalytic construction of spirooxindole naphthoquinones through Michael/hemiketalization using l-proline derived bifunctional thiourea

Diverse bispiro-3,4-dihydropyrans consisting of oxindole moieties with three contiguous chiral centers and vicinal quaternary stereocenters were synthesized with very good yields of up to 92% and excellent enantioselectivity of up to 99% ee by using a proline-derived thiourea organocatalyst. © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Asian Journal of Organic Chemistry

Asymmetric Organocatalytic Assembly of Oxindoles Fused with Spiro-3,4-dihydropyrans with Three Contiguous Stereocenters Consisting of Vicinal Quaternary Centers

ChemInform

ChemInform Abstract: Antiinflammatory and Antidiabetic Naphthaquinones from an Endophytic Fungus Dendryphion nanum (Nees) S. Hughes.

Journal of Medicinal Chemistry

A Potent Small-Molecule Inhibitor of the MDM2–p53 Interaction (MI-888) Achieved Complete and Durable Tumor Regression in Mice

Journal of the American Chemical Society

Highly Efficient Hydrogen-Bonding Catalysis of the Diels–Alder Reaction of 3-Vinylindoles and Methyleneindolinones Provides Carbazolespirooxindole Skeletons

Nature Communications

Diversity-oriented synthesis as a tool for the discovery of novel biologically active small molecules

Journal	Data powered by TypesetRSC Advances
Publisher	Data powered by TypesetRoyal Society of Chemistry
ISSN	20462069
Open Access	No