[3+2] Cycloadditions of α-acyl ketene dithioacetals with propargylamines: pyrrole synthesis in water

Ren, Chuan-Qing; Di, Chong-Hui; Zhao, Yu‐Long; Zhang, Jingping

doi:10.1016/j.tetlet.2013.01.020

Cited by 13 publications

(8 citation statements)

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“…When the reaction was performed in the presence of K 2 CO 3 , pyrroles 474 bearing a carbonyl group in position C2 were selectively formed, while in absence of a base, the formation of 2-EtS-pyrroles 475 was favored (Scheme 100). 289 Another efficient synthesis of 1,2,3,5-tetrasubstituted pyrroles 478 has been described by Wan and co-workers in 2013. Imines 476 were treated with N-propargylamines 477 in the presence of LiHMDS as base and PMDTA as the additive in THF affording pyrroles 478 in good yields (Scheme 101).…”

Section: Miscellaneous Metal-free Synthesis Of Pyrrolesmentioning

confidence: 99%

Synthesis and Reactivity of Propargylamines in Organic Chemistry

et al. 2017

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Propargylamines are a versatile class of compounds which find broad application in many fields of chemistry. This review aims to describe the different strategies developed so far for the synthesis of propargylamines and their derivatives as well as to highlight their reactivity and use as building blocks in the synthesis of chemically relevant organic compounds. In the first part of the review, the different synthetic approaches to synthesize propargylamines, such as A couplings and C-H functionalization of alkynes, have been described and organized on the basis of the catalysts employed in the syntheses. Both racemic and enantioselective approaches have been reported. In the second part, an overview of the transformations of propargylamines into heterocyclic compounds such as pyrroles, pyridines, thiazoles, and oxazoles, as well as other relevant organic derivatives, is presented.

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Section: Miscellaneous Metal-free Synthesis Of Pyrrolesmentioning

confidence: 99%

Synthesis and Reactivity of Propargylamines in Organic Chemistry

et al. 2017

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Section: Heteroannulation Reactions Via Ketene Ns-acetalsmentioning

confidence: 99%

“…Water (at reflux without an external base) has also been proven to be a suitable solvent for the above reaction (Table , reaction times and yields in parentheses) . Based on either the amount of amine , or the solvent applied, both the amine and hydroxide ion generated in situ can play the role of a nucleophile in deacylation as described in Scheme . 3-Phenylprop-2-yn-1-amine is also a suitable choice for [3 + 2] annulation, and this reaction has been successfully expanded to include the conversion of vinylogous thiol esters to the corresponding substituted pyrroles …”

Section: Heteroannulation Reactions Via Ketene Ns-acetalsmentioning

confidence: 99%

“…In comparison, the synthetic applications of ketene N , S -acetal has not been well explored. Taking account of the intrinsic nucleophilicity, distinctive combination of multiple reactive sites, and configurational flexiblility of ketene N , S -acetals in both polar and nonpolar media (Figure ), ,, further research on ketene N , S -acetals, as the biggest family in push–pull alkenes, may need to be focused on several topics, including (1) synthetic applications of cinnamoyl ketene N , S -acetals in annulation and multicomponent reactions, (2) biomass-derived building blocks as electrophiles, (3) synthetic applications of ketene N , S -acetals having a secondary amino group on the acetal end, , (4) transition-metal-catalyzed reaction (for example, C–H functionalization at the acceptor end), and (5) enantioselective cyclization reactions. In any case, efficient synthesis and synthetic applications of new ketene N , S -acetal species (for example, imino ketene N , S -acetals) are still the main themes of ketene N , S -acetal chemistry.…”

Section: Perspectives and Conclusionmentioning

confidence: 99%

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Chemistry of Ketene N,S-Acetals: An Overview

et al. 2016

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Push-pull alkenes, which bear electron-donating and -accepting group(s) at both termini of a C═C double bond, respectively, are of interest not only for their unique electronic properties but also for their importance as versatile building blocks in organic synthesis. In the world of ketene acetals having the push-pull alkene skeleton, ketene N,S-acetal is most likely the biggest family according to the number and types of these compounds. The first ketene N,S-acetal compound was reported in 1956. As a cyclic ketene N,S-acetal compound, nithiazine, the first lead structure of neonicotinoid insecticides, was reported in 1978. The characteristics of ketene N,S-acetals, which have the structural feature of ketene S,S-acetals and enaminones, make them versatile and easy to use, especially in cyclization and multicomponent reactions for the synthesis of various heterocyclic systems and related natural products. There has been an increasing wealth of information about the synthesis and synthetic applications of ketene N,S-acetals, especially, in recent years. This review provides comprehensive knowledge on the chemistry of ketene N,S-acetals.

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“…Ren and coworkers have synthesized a range of 2,3,4-trisubstituted-and 1,2,3,4-tetrasubstituted pyrroles via deacetylative [3 + 2] cycloaddition of α-acyl ketene dithioacetals or related substrates with commercially available propargyl amines as 1,3-dipole in aqueous media [46]. Most of the reactions do not need any external base.…”

Section: Formation Of Pyrrole Pyrrolidine and Pyrrolidinone Ringsmentioning

confidence: 99%