2-Formylpyrroles as Building Blocks in a Divergent Synthesis of Pyrrolizines

Martínez-Mora, Eder I.; Caracas, Miguel A.; Escalante, Carlos H.; Espinoza‐Hicks, José C.; Quiroz-Florentino, Héctor; Delgado, Francisco; Tamariz, Joaquı́n

doi:10.1055/s-0035-1561331

Cited by 11 publications

(4 citation statements)

References 9 publications

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“…In the current investigation, the nitrogen atom of the 2-formylpyrrole ring was incorporated into the C-2 position of the alkyl (Z)-3-(dimethylamino)propenoate-equivalent (1, Y = O, Z = CO 2 R, Scheme 1d), the (Z)-1-aryl-3-(dimethylamino)prop-2-en-1-one-equivalent (2, Y = O, Z = COAr, Scheme 1d), and the (Z)-3-(dimethylamino)acrylonitrile-equivalent (3, Y = O, Z = CN) (Scheme 1d), followed by the cyclization process in the presence of ammonium acetate to provide the corresponding pyrrolo[1,2-a]pyrazines 4. It was assumed that 2-formylpyrrole (6) can serve as a building block for the divergent synthesis of substituted pyrrolizines [30,39] and pyrrolo [1,2-a]pyrazines [30] to furnish the desired pyrrole-fused aza-bridged heterocyclic derivatives.…”

Section: Chemistrymentioning

confidence: 99%

“…In the current investigation, the nitrogen atom of the 2-formylpyrrole ring was incorporated into the C-2 position of the alkyl (Z)-3-(dimethylamino)propenoate-equivalent ( 6) can serve as a building block for the divergent synthesis of substituted pyrrolizines [30,39] and pyrrolo [1,2-a]pyrazines [30] to furnish the desired pyrrole-fused aza-bridged heterocyclic derivatives.…”

Section: Chemistrymentioning

confidence: 99%

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Pyrrole-Based Enaminones as Building Blocks for the Synthesis of Indolizines and Pyrrolo[1,2-a]pyrazines Showing Potent Antifungal Activity

Miranda-Sánchez,

Escalante,

Andrade-Pavón

et al. 2023

Molecules

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As a new approach, pyrrolo[1,2-a]pyrazines were synthesized through the cyclization of 2-formylpyrrole-based enaminones in the presence of ammonium acetate. The enaminones were prepared with a straightforward method, reacting the corresponding alkyl 2-(2-formyl-1H-pyrrol-1-yl)acetates, 2-(2-formyl-1H-pyrrol-1-yl)acetonitrile, and 2-(2-formyl-1H-pyrrol-1-yl)acetophenones with DMFDMA. Analogous enaminones elaborated from alkyl (E)-3-(1H-pyrrol-2-yl)acrylates were treated with a Lewis acid to afford indolizines. The antifungal activity of the series of substituted pyrroles, pyrrole-based enaminones, pyrrolo[1,2-a]pyrazines, and indolizines was evaluated on six Candida spp., including two multidrug-resistant ones. Compared to the reference drugs, most test compounds produced a more robust antifungal effect. Docking analysis suggests that the inhibition of yeast growth was probably mediated by the interaction of the compounds with the catalytic site of HMGR of the Candida species.

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Section: Chemistrymentioning

confidence: 99%

“…In the current investigation, the nitrogen atom of the 2-formylpyrrole ring was incorporated into the C-2 position of the alkyl (Z)-3-(dimethylamino)propenoate-equivalent ( 6) can serve as a building block for the divergent synthesis of substituted pyrrolizines [30,39] and pyrrolo [1,2-a]pyrazines [30] to furnish the desired pyrrole-fused aza-bridged heterocyclic derivatives.…”

Section: Chemistrymentioning

confidence: 99%

Pyrrole-Based Enaminones as Building Blocks for the Synthesis of Indolizines and Pyrrolo[1,2-a]pyrazines Showing Potent Antifungal Activity

Miranda-Sánchez,

Escalante,

Andrade-Pavón

et al. 2023

Molecules

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“…Additional intramolecular cross-coupling reactions were carried out by utilizing dimethyl malonates 8k and 8l, which were prepared through the N-benzylation of 16c with benzyl bromides 14b and 14d, respectively (Scheme 5). Pyrrole 16c was synthesized by Knoevenagel reaction of 13a with dimethyl malonate [42]. The Pd(0)-catalyzed cyclization of 8k and 8l required a temperature of 140 °C, but provided pyrrolo[2,1-a]isoindoles 18d and 18e, respectively, in good yields.…”

Section: Cyclization Via An Intramolecular Heck Arylation Reactionmentioning

confidence: 99%

“…Due to our interest in transforming simple five-membered heterocycles into natural products [40,41] and complex azapolycyclic structures [42], we herein combined both approaches shown in Scheme 1 to design the construction of pentacycles 11, after carrying out an uncommon but highly diastereoselective Diels-Alder cycloaddition followed by a coupling reaction. This route also allowed out the aromatization of Scheme 1: Synthetic approaches for the preparation of pyrrolo-fused aza-hetero polycyclic frames.…”

Section: Introductionmentioning

confidence: 99%

Highly selective Diels–Alder and Heck arylation reactions in a divergent synthesis of isoindolo- and pyrrolo-fused polycyclic indoles from 2-formylpyrrole

Escalante

Martínez-Mora

Espinoza‐Hicks

et al. 2020

Beilstein J. Org. Chem.

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A highly regio-, chemo- and stereoselective divergent synthesis of isoindolo- and pyrrolo-fused polycyclic indoles is herein described, starting from 2-formylpyrrole and employing Diels–Alder and Heck arylation reactions. 3-(N-Benzyl-2-pyrrolyl)acrylates and 4-(pyrrol-2-yl)butenones underwent a highly endo-Diels–Alder cycloaddition with maleimides to furnish octahydropyrrolo[3,4-e]indoles, which served as precursors in the regioselective synthesis of aza-polycyclic skeletons via an intramolecular Heck arylation reaction. Through the latter reaction, the 3-(N-benzyl-2-pyrrolyl)acrylates give rise to 3-(pyrrolo[2,1-a]isoindol-3-yl)acrylates. A further oxidative aromatization of the polycyclic intermediates provides the corresponding polycyclic pyrrolo-isoindoles and isoindolo-pyrrolo-indoles. A theoretical study on the stereoselective Diels–Alder reactions, carried out by calculating the endo/exo transition states, revealed the assistance of non-covalent interactions in governing the endo stereocontrol.

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Organocatalytic Enantioselective Friedel‐Crafts Alkylation Reactions of Pyrroles

et al. 2021

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Substituted and annulated pyrroles containing chiral centers are potentially accessible by means of an organocatalytic enantioselective Friedel-Crafts alkylation (FCA) reaction. They are interesting compounds because of their abundant natural occurrence and their different biological activities. In comparison to indoles, for which a myriad of asymmetric procedures involving the FCA have been developed, pyrroles have been relatively less used as nucleophilic counterparts in this reaction. However, in the last two decades, huge synthetic efforts have been performed around this interesting asymmetric transformation and several methodologies have been devised. In this context, this review article provides a general overview of the organocatalytic enantioselective FCA chemistry of pyrroles, which has not been revised to date. Reactions 2.4. Brønsted Acid Catalyzed Intramolecular FCA Reactions 3.Organocatalytic FCA Reactions with Dihydroindoles 4.Conclusions and Outlook

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2-Formylpyrroles as Building Blocks in a Divergent Synthesis of Pyrrolizines

Cited by 11 publications

References 9 publications

Pyrrole-Based Enaminones as Building Blocks for the Synthesis of Indolizines and Pyrrolo[1,2-a]pyrazines Showing Potent Antifungal Activity

Pyrrole-Based Enaminones as Building Blocks for the Synthesis of Indolizines and Pyrrolo[1,2-a]pyrazines Showing Potent Antifungal Activity

Highly selective Diels–Alder and Heck arylation reactions in a divergent synthesis of isoindolo- and pyrrolo-fused polycyclic indoles from 2-formylpyrrole

Organocatalytic Enantioselective Friedel‐Crafts Alkylation Reactions of Pyrroles

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