An efficient diastereoselective rhodium catalyzed synthesis of indolines possessing two contiguous tetrasubstituted carbon centers has been achieved with good to excellent yields using ortho-vinylanilines and iminocarbenes derived from N-sulfonyl-1,2,3-triazoles. The reaction affords excellent cis-diastereoselectivity through the initial formation of a N-ylide followed by intramolecular trapping with unactivated alkenes via an ene-type reaction with a well-organized transition state, namely intramolecular carbenylative amination of alkenes. The developed transformation was further extended to the successful synthesis of tricyclic compounds, imidazoindolines, through reduction and hypervalent iodine mediated oxidative cyclization. © 2016 The Royal Society of Chemistry.

Pazhamalai Anbarasan

Department Of Chemistry

Angula Chandra Shekar Reddy

carbon

catalysis

Hydrocarbons

Iodine compounds

Rhodium

Stereoselectivity

Diastereo-selectivity

Diastereoselective

Diastereoselective synthesis

Hypervalent iodine

INTRAMOLECULAR TRAPPING

OXIDATIVE CYCLIZATION

RHODIUM-CATALYZED SYNTHESIS

TRICYCLIC COMPOUNDS

Cyclization

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

Chemical Science

An efficient cascade Rh(ii) and Yb(iii) catalyzed transannulation of N-sulfonyl-1,2,3-triazoles with β-naphthols has been accomplished for the synthesis of substituted naphthofurans in good yields. The reaction involves the initial rhodium catalyzed insertion of azavinyl carbene into the O-H bond followed by ytterbium catalyzed annulative C-C bond formation and concomitant aerial oxidation. The developed reaction was successfully extended to phenols to afford substituted benzofurans. Furthermore, the synthetic utility of the method was demonstrated through the synthesis of important polyhetero aromatic compounds. © 2019 The Royal Society of Chemistry.

Chemical Communications

Cascade Rh(ii) and Yb(iii) catalyzed synthesis of substituted naphthofurans: Via transannulation of N -sulfonyl-1,2,3-triazoles with β-naphthols

Efficient and general copper catalyzed oxidative cyclization of ortho-vinylaniline has been accomplished employing N-tosylhydrazone as coupling partner. Various substituted quinoline derivatives of biological importance were achieved in good to excellent yield. The important features are the high functional group tolerates, up-gradation to gram scale synthesis and possible one-pot synthesis of quinoline from corresponding carboxaldehyde. Synthetic potential of the obtained quinoline derivatives was demonstrated through C-H bond functionalization reaction. Furthermore, preliminary mechanistic investigation revealed the possible generation of non-stabilized diazo compound and imine derivative as potential intermediates as well as copper catalyzed electrocyclic reaction and oxidative aromatization. © 2018 Elsevier Inc.

Journal of Catalysis

Copper catalyzed oxidative coupling of ortho-vinylanilines with N-tosylhydrazones: Efficient synthesis of polysubstituted quinoline derivatives

A general and efficient one-pot aminoethylation of substituted indoles/pyrroles was accomplished for the synthesis of various tryptamine derivatives employing a combination of alkynes and sulfonyl azides as readily accessible aminoethylating agents. The reaction features a successful integration of copper-catalyzed alkyne and azide cycloaddition to N-sulfonyl-1,2,3-triazole, rhodium-catalyzed selective insertion of α-iminocarbenes onto the C3-H bond of indoles, and reduction of the resultant enamides to tryptamine derivatives employing either NaCNBH3 or palladium catalyst, in one-pot. The reaction also showed excellent functional-group tolerance and allowed the synthesis of various substituted tryptamines in good to excellent yield. This transformation constitutes a one-pot formal regioselective functionalization of terminal alkynes. Utility of the synthesized tryptamine was further demonstrated in the synthesis of dihydro-β-carboline and tryptoline. © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

Chemistry - A European Journal

One-Pot Aminoethylation of Indoles/Pyrroles with Alkynes and Sulfonyl Azides

Rhodium-catalyzed transannulation of N-sulfonyl-1,2,3-triazoles with vinyl ether has been accomplished for the synthesis of various polysubstituted pyrroles. The present method allows the synthesis of mono-, di-, and trisubstituted pyrroles with appropriate substitutions. Furthermore, the developed methodology was applied in the formal synthesis of neolamellarin A, an antitumor agent. © 2014 American Chemical Society.

Journal of Organic Chemistry

Rhodium-catalyzed transannulation of 1,2,3-triazoles to polysubstituted pyrroles

Suitably substituted electron-deficient 1,2,3-triazoles exist in equilibrium with their ring-opened α-diazoimine tautomers. This phenomenon was used to facilitate the generation of synthetically useful metallo azavinyl carbene intermediates. In this short review, we describe recent developments in the transition-metal-catalyzed decomposition of electron-deficient (annulated) 1,2,3-triazoles to form metallo azavinyl carbenes, and their application in the synthesis of highly functionalized nitrogen-based heterocycles and building blocks through various synthetic transformations, such as transannulation, cyclopropanations, insertion reactions, ylide formation/rearrangements, and ring expansions. 1 Introduction 2 Ring-Chain Isomerism 3 Synthesis of N-Sulfonyl-1,2,3-triazoles 4 Denitrogenative Transformations of 1,2,3-Triazoles 4.1 Transannulations with Nitriles and Alkynes 4.2 Transannulations with Alkenes or Carbonyl Compounds 4.3 Transannulations with (Hetero)cumulenes or 1,3-Dienes 4.4 Insertions into X-H or C-X bonds 4.5 Rearrangement/Ring Expansion 4.6 Miscellaneous Transformations 5 Summary and Outlook. © Georg Thieme Verlag Stuttgart - New York.

Synthesis (Germany)

Recent advances in transition-metal-catalyzed denitrogenative transformationsÂ- of 1,2,3-triazoles and related compounds

Reference Module in Chemistry, Molecular Sciences and Chemical Engineering

Cambridge Crystallographic Data Centre (CCDC)

Leukemia

Human NUP98-IQCG fusion protein induces acute myelomonocytic leukemia in mice by dysregulating the Hox/Pbx3 pathway

Rhodium catalyzed diastereoselective synthesis of 2,2,3,3-tetrasubstituted indolines from: N -sulfonyl-1,2,3-triazoles and ortho -vinylanilines

Journal	Data powered by TypesetChemical Science
Publisher	Data powered by TypesetRoyal Society of Chemistry
ISSN	20416520
Open Access	Yes