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.

Pazhamalai Anbarasan

Department Of Chemistry

Shanmugam Rajasekar

catalysis

1 ,2 ,3-TRIAZOLES

ANTI-TUMOR AGENTS

Formal synthesis

Rhodium-catalyzed

Transannulation

VINYL ETHERS

Rhodium

1,2,3 TRIAZOLE DERIVATIVE

antineoplastic agent

NEOLAMELLARIN A

pyrrole derivative

unclassified drug

triazole derivative

annulation reaction

antineoplastic activity

article

Cyclization

drug synthesis

reaction time

chemical structure

chemistry

synthesis

Antineoplastic Agents

Molecular Structure

Pyrroles

Triazoles

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

Journal of Organic Chemistry

An efficient and novel rhodium-catalyzed transannulation of N-sulfonyl-1,2,3-triazoles with in situ generated o-quinone methides (o-QMs) from 2-hydroxybenzyl alcohols has been achieved for the synthesis of substituted benzopyrans in good yields. The developed reaction involves nucleophilic attack of o-QM to α-imino rhodium carbenoid to generate a carbonyl ylide followed by 6π-electrocyclization and isomerization. Furthermore, the utility of the methodology was demonstrated in the one-pot synthesis and construction of polyheteroaromatics. Copyright © 2018 American Chemical Society.

Organic Letters

Rhodium Catalyzed Synthesis of Benzopyrans via Transannulation of N-Sulfonyl-1,2,3-triazoles with 2-Hydroxybenzyl Alcohols

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.

Fulltext

Chemical Science

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

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

An efficient rhodium catalyzed direct arylation of α-diazoimines, generated from readily accessible 1,2,3-triazole, has been accomplished for the synthesis of 2,2-diaryl enamides. The reaction involves the chemo- and regioselective insertion of rhodium azavinyl carbene into aromatic C(sp 2)-H bonds. Utility of the developed methodology was demonstrated in the synthesis of indole and tetrahydroisoquinoline frameworks. © 2014 American Chemical Society.

Rhodium catalyzed direct arylation of α-diazoimines

Angewandte Chemie International Edition

Cover Picture: Regioselectively Functionalized Pyridines from Sustainable Resources (Angew. Chem. Int. Ed. 24/2013)

Spotlights on our sister journals: Angew. Chem. Int. Ed. 50/2010

Nanotechnology

Natural Product Communications

Synthesis of Neolamellarin A, an Inhibitor of Hypoxia-Inducible Factor-1

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

Journal	Data powered by TypesetJournal of Organic Chemistry
Publisher	Data powered by TypesetAmerican Chemical Society
ISSN	00223263
Open Access	No