Synthesis of indolines via a domino Cu-catalyzed amidation/cyclization reaction.

Org Lett

Department of Chemistry, Massachusetts Institute of Technology, Cambridge, Massachusetts 02139, USA.

Published: July 2008

A highly efficient one-pot procedure for the synthesis of indolines and their homologues based on a domino Cu-catalyzed amidation/nucleophilic substitution reaction has been developed. Substituted 2-iodophenethyl mesylates and related compounds afforded the corresponding products in excellent yields. No erosion of optical purity was observed when transforming enantiomerically pure mesylates under the reaction conditions.

Download full-text PDF

Source
http://www.ncbi.nlm.nih.gov/pmc/articles/PMC2489202PMC
http://dx.doi.org/10.1021/ol8008792DOI Listing

Publication Analysis

Top Keywords

synthesis indolines
8
domino cu-catalyzed
8
indolines domino
4
cu-catalyzed amidation/cyclization
4
amidation/cyclization reaction
4
reaction highly
4
highly efficient
4
efficient one-pot
4
one-pot procedure
4
procedure synthesis
4

Similar Publications

Organocatalytic, enantioselective decarboxylative Mannich reactions of α,β-unsaturated β'-ketoacids and isatin -Boc imines, to give the corresponding 3-carbamoyl-2-oxindole derivatives, were developed. Subsequent N-deprotection and diastereoselective, intramolecular, aza-Michael reaction of the free amine provides previously unreported spiro[indoline-3,2'-piperidine]-2,4'-diones.

View Article and Find Full Text PDF

In the current study, new pyranopyrazole analogs (9a-d and 10a-d) were synthesized through a one-pot condensation reaction of 2-arylacetohydrazide. The inhibitory abilities were investigated against the xanthine oxidase (XO) enzyme through experimental and molecular docking analyses. The synthesis studies were based on ultrasound-mediated condensation reactions of four-component containing 2-arylacetohydrazide, ethyl acetoacetate, indoline-2,3-dione, and ethyl 2-cyanoacetate/malononitrile in various solvents and catalysts to yield pyranopyrazole analogs (9a-d and 10a-d) in a short reaction time and remarkably favorable yields ranging from 79% to 92%.

View Article and Find Full Text PDF

An unprecedented formal [1+5] cyclization of indoline-derived azadienes with 1,3,5-triazinanes has been realized, providing a facile access to biologically important indoline-spiro-hexahydropyrimidines with good to excellent yields (up to 99 % yield). Different from previous reports, this is the first study that indoline-derived azadienes could participate in cyclizations as one-atom synthons. This methodology is also distinguished by not involving any additive or catalyst, readily available starting materials, wide range of substrate applicability, operational simplicity and simultaneously reassembling two C-N and two C-C bonds in one-step reaction.

View Article and Find Full Text PDF

Photo-Promoted Construction of 3-Spiro-2-sulfonylimino-indoline Skeletons via Cascade Reaction.

Org Lett

January 2025

State Key Laboratory of Chemical Resource Engineering, Department of Organic Chemistry, College of Chemistry, Beijing University of Chemical Technology, Beijing 100029, People's Republic of China.

The cascade reaction of 3-diazo-2-sulfonyliminoindolines and -methoxymethyl--[(trimethylsilyl)methyl]benzylamines generates 2-sulfonylimino-1',3',4',6'-tetrahydro-2'-spiro[indoline-3,5'-pyrimidine] and spiro[indoline-3,3'-pyrrolidine] derivatives simultaneously under the catalysis of TFA and blue light irradiation. Their formation mechanisms were proposed on the basis of isotope-labeled experiments and HRMS analysis of the controlled experiment mixture, showing new reaction pathways. The current reaction provides a new strategy for the synthesis of biologically important spiro[indoline-3,3'-pyrrolidine]-2-one derivatives.

View Article and Find Full Text PDF

We report herein an efficient and site-selective electrophilic trifluoromethylthiolation of indolines. In the absence of any catalyst or additive, C5-selective trifluoromethylthiolation could proceed at room temperature. With palladium used as the catalyst, the selectivity was reversed completely, giving C7-selecive trifluoromethylthiolated products.

View Article and Find Full Text PDF

Want AI Summaries of new PubMed Abstracts delivered to your In-box?

Enter search terms and have AI summaries delivered each week - change queries or unsubscribe any time!