Synthesis of cyclic analogues of hexamethylenebis(3-pyridine)amide (HMBPA) in a one-pot process

Zamudio‐Medina, Angel; García‐González, Ma. Carmen; Gutiérrez-Carrillo, Atilano; González‐Zamora, Eduardo

doi:10.1016/j.tetlet.2014.12.018

Cited by 17 publications

(8 citation statements)

References 29 publications

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“…Thus, it can be found in the literature of our own reports [10,11,12,13,14,15], which are previous works to the present one, and in the above-mentioned methodology from the Couture’s group [7], which is a close work to the present one, in which Falipamil ( 1 ) and some of its analogues ( 2 – 3 ) are synthesized efficiently, but via a stepwise strategy, resulting in larger times and generally using harsh conditions. Moreover, pioneering works from Bienaymé and Zhu [16,17] allowed the synthesis of pyrrolo[3,4- b ]pyridin-5-ones via a cascade process (Ugi-3CR/aza Diels-Alder/ N -acylation/aromatization) in good yields, short reaction times, and under relatively milder conditions with respect to stepwise methods.…”

Section: Introductionmentioning

confidence: 84%

“…In this context, we have reported some one-pot syntheses on a series of novel, fused, polyheterocyclic pyrrolo[3,4- b ]pyridin-5-one-based compounds via an Ugi-3CR/aza Diels-Alder/ N -acylation/aromatization cascade sequence combined with further cyclization processes like free-radical mediated [10], Pummerer [11], Pictet-Spengler [12], and Pomeranz-Fritsch [13]. In the same way, we developed an oxidative [14] and a repetitive version [15] of this robust one-pot cascade process (Ugi-3CR/aza Diels-Alder/ N -acylation/aromatization). Additionally, by using this methodology (one-pot approach), diverse aza-analogues of natural products, such as (±)-Nuevamine, (±)-Lennoxamine, and Magallanesine, were synthesized successfully [13].…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of Polyheterocyclic Pyrrolo[3,4-b]pyridin-5-ones via a One-Pot (Ugi-3CR/aza Diels-Alder/N-acylation/aromatization/SN2) Process. A Suitable Alternative towards Novel Aza-Analogues of Falipamil

et al. 2018

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We describe the one-pot synthesis of twenty polyheterocyclic pyrrolo[3,4-b]pyridin-5-ones via a cascade process (Ugi-3CR/aza Diels-Alder/N-acylation/aromatization) in 20 to 95% overall yields, as well as four pharmacologically promising analogues via an improved cascade process (Ugi-3CR/aza Diels-Alder/N-acylation/aromatization/SN2): two piperazine-linked pyrrolo[3,4-b]pyridin-5-ones in 33 and 34%, and a couple of Falipamil aza-analogues in 30 and 35% overall yields. It is worth highlighting the good substrate scope found, because final products are furnished with alkyl, aryl, and heterocyclic substituents. The use of chain-ring tautomerizable isocyanides (as key reagents for the Ugi-type three component reaction) allowed for a rapid and efficient assembly of the polysubstituted oxindoles, which were used in situ toward the complex products, conferring features like robustness, sustainability, and the one-pot approach to this synthetic methodology.

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Section: Introductionmentioning

confidence: 84%

Section: Introductionmentioning

confidence: 99%

Synthesis of Polyheterocyclic Pyrrolo[3,4-b]pyridin-5-ones via a One-Pot (Ugi-3CR/aza Diels-Alder/N-acylation/aromatization/SN2) Process. A Suitable Alternative towards Novel Aza-Analogues of Falipamil

et al. 2018

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“…[74] The combination of readily available salicylaldehydes, Meldrum's acid, amine, propargyloxy aldehyde, Isocyanide, aryl azide followed a tandem Knoevenagel/Ugi/click sequence in the presence of Cu(OAc) 2 and sodium ascorbate in ethanol In 2014, Eduardo González-Zamora and his group members reported the synthesis of various spacer linked bis pyrrolo[3,4b]pyridines 74 through post-functionalization of U-3CR adduct with the aza-Diels-Alder reaction in a single pot. [75] Initially, the microwave-assisted reaction of hexamethylenediamine, aldehydes, and isocyanides were carried out using scandium (III) triflate catalyst in benzene solvent to afford U-3CR adduct 73.…”

Section: Ugi-based Imcrs For the Synthesis Of Spacer-linked Bhcsmentioning

confidence: 99%

One‐Pot Construction of Bis‐Heterocycles through Isocyanide Based Multicomponent Reactions

Bhat

2020

ChemistrySelect

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Bis‐heterocycles (BHCs) are hybrid molecules comprising two linked, bound, spacer, or fused heterocyclic skeletons. In recent years, these compounds have attracted increased attention of scientific communities because of their improved potential applications than their discrete units. The emergence of numerous synthetic protocols utilizing Isocyanide as one of the components in multicomponent reactions has unleashed innumerable openings to design and synthesize diverse heterocyclic scaffolds and thus Isocyanide based multicomponent reactions (IMCRs) are leading today's MCR chemistry. To date, there has not been any exclusive review on the construction of BHCs via direct IMCRs or its combination with other reaction sequences in one‐pot. This article presents the first overview of IMCRs such as Ugi, Groebke‐Blackburn‐Bienaymé (GBBR), their sequential combination with other reactions, and new IMCRs established for the one‐pot synthesis of BHCs in the last two decades.

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“…González-Zamora et al (Zamudio-Medina et al, 2015 ) have described a one-pot, Ugi-4CR for the synthesis of cyclic analogs of hexamethylenebis(3-pyridine)amide (HMBPA) 10e in low yields. After reaction of diamine 10a , aldehydes 10b , and isocyanoacetamides 10c , cycloaddition and ring opening reaction with maleic anhydride 10d was performed under MW irradiation using Sc(OTf) 3 as a catalyst in benzene (Scheme 5 ).…”

Section: Fused Heterocyclesmentioning

confidence: 99%

Post-Ugi Cyclization for the Construction of Diverse Heterocyclic Compounds: Recent Updates

Bariwal¹,

Kaur

Voskressensky

et al. 2018

Front. Chem.

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Multicomponent reactions (MCRs) have proved as a valuable tool for organic and medicinal chemist because of their ability to introduce a large degree of chemical diversity in the product in a single step and with high atom economy. One of the dominant MCRs is the Ugi reaction, which involves the condensation of an aldehyde (or ketone), an amine, an isonitrile, and a carboxylic acid to afford an α-acylamino carboxamide adduct. The desired Ugi-adducts may be constructed by careful selection of the building blocks, opening the door for desired post-Ugi modifications. In recent times, the post-Ugi transformation has proved an important synthetic protocol to provide a variety of heterocyclic compounds with diverse biological properties. In this review, we have discussed the significant advancements reported in the recent literature with the emphasis to highlight the concepts and synthetic applications of the derived products along with critical mechanistic aspects.

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Synthesis of cyclic analogues of hexamethylenebis(3-pyridine)amide (HMBPA) in a one-pot process

Cited by 17 publications

References 29 publications

Synthesis of Polyheterocyclic Pyrrolo[3,4-b]pyridin-5-ones via a One-Pot (Ugi-3CR/aza Diels-Alder/N-acylation/aromatization/SN2) Process. A Suitable Alternative towards Novel Aza-Analogues of Falipamil

Synthesis of Polyheterocyclic Pyrrolo[3,4-b]pyridin-5-ones via a One-Pot (Ugi-3CR/aza Diels-Alder/N-acylation/aromatization/SN2) Process. A Suitable Alternative towards Novel Aza-Analogues of Falipamil

One‐Pot Construction of Bis‐Heterocycles through Isocyanide Based Multicomponent Reactions

Post-Ugi Cyclization for the Construction of Diverse Heterocyclic Compounds: Recent Updates

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