Intermolecular coupling of alkynes, isocyanates, and acyl chlorides: an efficient method for the synthesis of 5-hydroxypyrrol-2(5H)-ones

Kanno, Ken‐ichiro; Ren, Shenyong; Li, Yanzhong; Nakajima, Kiyohiko; Takahashi, Tamotsu

doi:10.1016/j.tetlet.2007.10.096

Cited by 14 publications

(3 citation statements)

References 18 publications

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“…The photochemical isomerization then cyclisation of (E)-gketo-a,b-unsaturated amides (113) has been used to synthesize g-hydroxypyrrolidinones (114). This was applied to the synthesis of jatropham (115) (Scheme 26).…”

Section: Cyclization Of 4-ketoamides Into G-hydroxylactamsmentioning

confidence: 99%

“…111,112 The reaction of diethylzirconocene with an alkyne (R 1 -C^C-R 2 : 199; R 1 ¼ alkyl, Ph or TMS; R 2 ¼ alkyl or Ph), an isocyanate (R 3 NCO; R 3 ¼ Ph, Bn, Bu or Ts) and an acyl chloride (R 4 COCl; R 4 ¼ Ph or Bu) proved to be an efficient method for the synthesis of 5-hydroxy-3-pyrrolin-2-ones 201 (Scheme 43B). 113 A new class of 5-substituted 3-pyrrolin-2-ones (203) that are cathepsin B inhibitors was synthesized exploiting a unique reaction cascade based on alkaline hydrolysis of the corresponding diethyl a-hydroxy-a-(b-propiolamide)malonates 202 (Scheme 44). 114 Diastereomerically pure bicyclic lactams 206 were obtained from phenylalaninol enamines 204 and glyoxal through the pyrrolinone 205 (Scheme 45).…”

Section: Oxidation Of 5-alkyl-3-pyrrolin-2-onesmentioning

confidence: 99%

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Chemistry and biology of non-tetramic γ-hydroxy-γ-lactams and γ-alkylidene-γ-lactams from natural sources

2009

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Natural products containing non-tetramic gamma-hydroxy-gamma-lactams and gamma-alkylidene-gamma-lactams are usually but not exclusively derived from the mixed polyketide-non-ribosomal peptide biosynthetic pathway. Often they are fungal metabolites, although some plant- and marine-derived exceptions exist. Owing to their unique structures and biological properties, they have gained interest in the chemical and biological communities. In this review, we aim to emphasize the structural originality of these compounds, their biological properties and the synthetic efforts developed to reach them; 157 references are cited.

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Section: Cyclization Of 4-ketoamides Into G-hydroxylactamsmentioning

confidence: 99%

Section: Oxidation Of 5-alkyl-3-pyrrolin-2-onesmentioning

confidence: 99%

Chemistry and biology of non-tetramic γ-hydroxy-γ-lactams and γ-alkylidene-γ-lactams from natural sources

2009

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“…Takahashi and co-workers reported a zirconium-mediated sequential one-pot coupling reaction of alkynes, isocyanates, and acyl chlorides to access γ-hydroxy-γ-butyrolactams (Scheme 35). 67 The reaction occurred with both symmetrical and unsymmetrical alkynes to regioselectively afford a single isomer. Diverse isocyanates and sterically hindered acyl chlorides were used without affecting the isolated yields.…”

Section: Sequential One-pot Coupling Of Alkynes Isocyanates and Acymentioning

confidence: 99%

Strategies To Access γ-Hydroxy-γ-butyrolactams

Mardjan

Parrain²,

Comméiras

2018

Synthesis

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α,β-Unsaturated γ-hydroxy-γ-butyrolactams are of a great interest due to their presence in designed pharmaceutical molecules and numerous natural products displaying a broad spectrum of biological activities. In addition, these five-membered heterocyclic compounds are also relevant and versatile building blocks in organic synthesis. In this context, strategies for the construction of these scaffolds has triggered considerable attention and this review highlights the progress in the formation of α,β-unsaturated γ-hydroxy-γ-butyrolactams (5-hydroxy-1,5-dihydro-2H-pyrrol-2-ones).1 Introduction2 Intramolecular Routes3 Intermolecular Routes4 Oxidation of Heterocyclic Compounds5 Miscellaneous6 Conclusion

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Iron‐Catalyzed Regioselective Hydroaryloxylation of CC Triple Bonds: An Efficient Synthesis of 2H‐1‐Benzopyran Derivatives

Liu

Liang

et al. 2009

Adv Synth Catal

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An efficient, regioselective, iron-catalyzed intramolecular hydroaryloxylation of 2-propargylphenols or naphthols is reported. The reactions proceed through an endo-dig cyclization to afford benzopyran or naphthopyran derivatives in good to high yields using ironA C H T U N G T R E N N U N G (III) chloride as the catalyst with the assistance of aniline in dimethylformamide (DMF).Keywords: benzopyrans; hydroaryloxylation; iron catalysis; naphthopyrans; regioselective cyclizationThe transition metal-catalyzed or -mediated intramolecular O À H addition across unsaturated C À C bonds represents one of the most effective and atom-economical routes to oxygen-containing heterocycles. [1] These catalysts include lanthanide, [1a-c] Pt, [1d,i] Ru, [1p] Au, [1d,g,m,r] Ag, [1k,n] Cu [1e] etc. Oxygen-containing heterocyclic moieties such as benzopyran rings represent key structural units of a variety of natural compounds with interesting biological activities.[2] Different synthetic approaches to these compounds were reported in the literature, such as metal-catalyzed intramolecular ring closure, [1,3] acid-mediated condensation [4] and others.[5] Due to the drawbacks of the reported methods, for example, low yields, requirement of a large excess amount of one of the reagents or high catalyst costs, the development of sustainable, environmentally friendly and less expensive catalysts to accomplish the carbon-heteroatom bond forming process is highly desired. As a result, iron-catalyzed C À C and C À X bond formation has attracted considerable attention, because iron compounds are usually less toxic, low priced and easy to synthesize. There have been a lot of reports concerning the Fe-catalyzed C À C forming reactions with the assistance of Grignard reagents. [6,7] In the past few years, Fe-catalyzed C À C and C À X bond forming reactions without the utilization of Grignard reagents have also appeared. [8,9] In the course of our ongoing study on the development of new, transition metal-catalyzed, selective heterocycle forming protocols, [10] we found that iron-catalyzed benzopyran ring formation was accomplished with high regioselectivity with the assistance of amines. Herein we would like to present our results of the iron-catalyzed regioselective synthesis of 2H-1-benzopyran derivatives by the intramolecular hydroaryloxylation of C C triple bonds.For intramolecular 2-propargylphenol hydro-A C H T U N G T R E N N U N G aryloxyA C H T U N G T R E N N U N G lations, there exist two possible pathways, namely exo-dig or endo-dig cyclization to five-or sixmembered rings according to Baldwins rules [11] (Scheme 1). Generally, metal-mediated hydroaryloxylation facilitates an exo-attack to give five-membered rings [1a-e,12] there is only one example of the six-membered ring formation catalyzed by Ru.[1p] It is therefore attractive to develop a metal-catalyzed, regioselective hydroaryloxylation for six-membered ring formation.Scheme 1.

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Intermolecular coupling of alkynes, isocyanates, and acyl chlorides: an efficient method for the synthesis of 5-hydroxypyrrol-2(5H)-ones

Cited by 14 publications

References 18 publications

Chemistry and biology of non-tetramic γ-hydroxy-γ-lactams and γ-alkylidene-γ-lactams from natural sources

Chemistry and biology of non-tetramic γ-hydroxy-γ-lactams and γ-alkylidene-γ-lactams from natural sources

Strategies To Access γ-Hydroxy-γ-butyrolactams

Iron‐Catalyzed Regioselective Hydroaryloxylation of CC Triple Bonds: An Efficient Synthesis of 2H‐1‐Benzopyran Derivatives

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