Synthesis and reactivity of pyrrolo[3,2-d][1,3]oxazine-2,4-dione. Access to new pyrrolo[3,2-e][1,4]diazepine-2,5-diones

Malcor, Jean‐Daniel; Brouillette, Yann; Graffion, Julien; Spielmann, Kim; Masurier, Nicolas; Maillard, Ludovic T.; Martinez, Jean; Lisowski, Vincent

doi:10.1016/j.tet.2014.05.046

Cited by 5 publications

(4 citation statements)

References 41 publications

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“…Our synthesis of racemic marinopyrrole A ( 1 ) began with the formation of bipyrrole 5 (Scheme ). This was achieved by condensation of aminopyrrole 3 8 and α‐keto ester 4 9 in 75 % yield. After conversion of both ester groups into the corresponding Weinreb amides (91 %), diamide 6 was treated with o ‐lithiated anisole 7 to give ketone 8 in one step in 86 % yield.…”

Section: Resultsmentioning

confidence: 99%

Exploration of the Bis(thio)urea‐Catalyzed Atropselective Synthesis of Marinopyrrole A

et al. 2016

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The marinopyrroles are a new class of natural products with highly interesting biomedical and structural features. We herein provide a concise, nitrogen‐protective‐group‐free synthesis of marinopyrrole A, constituting the as yet most efficient route. The presented studies elaborate a straightforward and mild chlorination protocol. Moreover, the first study towards the atropselective synthesis of marinopyrrole A, using chiral, C2‐symmetric bisthiourea catalysts, is presented.

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Section: Resultsmentioning

confidence: 99%

Exploration of the Bis(thio)urea‐Catalyzed Atropselective Synthesis of Marinopyrrole A

et al. 2016

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“…Diethyl N′ ,3‐Bipyrrole‐2,2′‐dicarboxylate (5): 6a Ethyl 3‐aminopyrrole‐2‐carboxylate hydrochloride8 ( 3 ; 1.91 g, 10.0 mmol, 1.0 equiv.) was dissolved in toluene (25 mL, 0.4 M ), and keto ester 4 9 (2.59 g, 12.00 mmol, 1.2 equiv.)…”

Section: Methodsmentioning

confidence: 99%

Thermal Evaluation of Diesel/Hydrogen Peroxide Fuel Blend

et al. 2015

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Thermal properties of fossil fuel are the key fundamental characteristics, which can distinguish any compound as a potential fuel. The performance of diesel fuel blend along with stability and solubility parameter designs are evaluated. The results from the experimental study indicate that the increase in hydrogen peroxide (H2O2) amount enhances the cetane number of diesel fuel blend significantly. However, the calorific value decreases as compared to pure diesel fuel. All values performed well according to the ASTM D‐975 diesel testing method. The thermodynamics of the prepared fuel blends also revealed that substantial solubility and diesel/H2O2 blend stability are provided even at lower temperatures. Such blends can be used as a feasible replacement of pure diesel fuel.

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“…Malcor et al prepared 3-(2-pyrrolyl)-5-methylhydantoin by the opening of an oxazine with the N-terminal moiety of alanine methyl ester. 186 This led to an ureido intermediate which cyclized in acidic medium into the hydantoin. The same group extended this procedure to the synthesis of thienylhydantoins from various amino acids.…”

Section: Use Of 11-carbonyldiimidazole (Cdi)mentioning

confidence: 99%

“…Anhydride bonds also represent activated scaffolds for amine substitution reactions and so formation of ureas. Malcor et al prepared 3-(2-pyrrolyl)-5-methylhydantoin by the opening of an oxazine with the N- terminal moiety of alanine methyl ester . This led to an ureido intermediate which cyclized in acidic medium into the hydantoin.…”

Section: - and 35-disubstituted Hydantoinsmentioning

confidence: 99%

Recent Advances in the Synthesis of Hydantoins: The State of the Art of a Valuable Scaffold

et al. 2017

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The review highlights the hydantoin syntheses presented from the point of view of the preparation methods. Novel synthetic routes to various hydantoin structures, the advances brought to the classical methods in the aim of producing more sustainable and environmentally friendly procedures for the preparation of these biomolecules, and a critical comparison of the different synthetic approaches developed in the last twelve years are also described. The review is composed of 95 schemes, 8 figures and 528 references for the last 12 years and includes the description of the hydantoin-based marketed drugs and clinical candidates.

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Synthesis and reactivity of pyrrolo[3,2-d][1,3]oxazine-2,4-dione. Access to new pyrrolo[3,2-e][1,4]diazepine-2,5-diones

Cited by 5 publications

References 41 publications

Exploration of the Bis(thio)urea‐Catalyzed Atropselective Synthesis of Marinopyrrole A

Exploration of the Bis(thio)urea‐Catalyzed Atropselective Synthesis of Marinopyrrole A

Thermal Evaluation of Diesel/Hydrogen Peroxide Fuel Blend

Recent Advances in the Synthesis of Hydantoins: The State of the Art of a Valuable Scaffold

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