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

Venkitasamy Kesavan

Department Of Biotechnology

Nandarapu Kumarswamyreddy

Kanduru Lokesh

3 ALKYNYL 3 INDOLE OXINDOLE DERIVATIVE

3 ALKYNYL PHENOL OXINDOLE DERIVATIVE

ANTIINFLAMMATORY AGENT

antimalarial agent

antineoplastic agent

chromene derivative

Copper

indole derivative

JP 8 G

MITOGEN ACTIVATED PROTEIN KINASE P38 INHIBITOR

NELIVAPTAN

NONNUCLEOSIDE REVERSE TRANSCRIPTASE INHIBITOR

NTD 609

OXINDOLE

phenol derivative

SPERMICIDAL AGENT

SPIROOXINDOLE DERIVATIVE

unclassified drug

Alkylation

article

Cyclization

drug structure

drug synthesis

FRIEDEL CRAFTS REACTION

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

Tetrahedron Letters

The synthesis of highly functionalized spirocarbocyclic oxindoles was accomplished for the first time, using a Hauser annulation strategy. A reaction between methyleneindolinones and arylsulfonylphthalides catalyzed by cesium carbonate gave access to a new class of biologically important spiro[indoline-3,2′-naphthalene] derivatives in very good yields. © 2017 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

European Journal of Organic Chemistry

Efficient Synthesis of Highly Functionalized Spirocarbocyclic Oxindoles through Hauser Annulation

A new synthetic strategy to construct spirooxindole-naphthopyran scaffold has been demonstrated via Friedel-Crafts type/hemiketalization of oxindole α-ketoester with 2-naphthol. Under the established reaction condition, quaternary chiral center at C3-position of oxindole has been created with very good asymmetric induction up to 98 % for a broad range of substrates. DFT calculations, which account for the stereochemical outcome, were performed. © 2016 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

ChemCatChem

Organocatalytic Enantioselective Assembly of Spirooxindole-naphthopyrans through Tandem Friedel-Crafts Type/Hemiketalization

3-Alkynyl-3-OBoc (Boc = tert-butoxycarbonyl) oxindole derivatives underwent a CuII-mediated stereo- and regioselective Friedel–Crafts alkylation/5-exo-dig-cyclization with 2-naphthols or cyclic 1,3-diketones. This gave spirooxindole [2,1-b]furan motifs in good to excellent yields under ambient conditions, and the process has a wide substrate scope. © 2016 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim

Stereoselective and Regioselective Assembly of Spirooxindole [2,1-b]furan Motifs through a Tandem Friedel–Crafts Alkylation/5-exo-dig-Cyclization

A new bifunctional squaramide organocatalyst derived from l-proline mediated the first enantioselective synthesis of dihydrospiro[indoline-3,4′-pyrano[2,3-c]pyrazole] derivatives in excellent enantioselectivity by reacting pyrazolones with isatylidine β,γ-unsaturated α-ketoester. This new catalyst outperformed widely used thioureas and squaramides in inducing enantioselectivity. © 2016 American Chemical Society.

Organic Letters

Enantioselective Synthesis of Dihydrospiro[indoline-3,4′-pyrano[2,3-c]pyrazole] Derivatives via Michael/Hemiketalization Reaction

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

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

Journal	Data powered by TypesetTetrahedron Letters
Publisher	Data powered by TypesetElsevier Ltd
ISSN	00404039
Open Access	No