Cyclizations of N-carbamoyl and N-thiocarbamoyl iminium ions leading to ring-fused heterocycles

Qarah, Ahmad; Klumpp, Douglas A.

doi:10.1016/j.tetlet.2016.09.026

Cited by 5 publications

(5 citation statements)

References 15 publications

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“…Hence, methods allowing simultaneous pyrrolidine ring closure and C–C (hetero)aryl bond formation are of a special interest. Most often this transformation is achieved by intramolecular Pictet‐Spengler reaction of 4‐aminocarbonyl compounds or their acetals possessing aryl moiety (Scheme , A) . However, only polycyclic pyrrolidine derivatives are available via this approach.…”

Section: Introductionmentioning

confidence: 99%

“…Most often this transformation is achieved by intramolecular Pictet-Spengler reaction of 4-aminocarbonyl compounds or their acetals possessing aryl moiety (Scheme 1, A). [6,21,23] How-ever, only polycyclic pyrrolidine derivatives are available via this approach. Intermolecular variants of such reactions allowing one-pot synthesis of 2-(hetero)arylpyrrolidines have received much less attention.…”

Section: Introductionmentioning

confidence: 99%

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Acid‐Catalyzed Cascade Reaction of 4‐Aminobutanal Derivatives with (Hetero)aromatic Nucleophiles: A Versatile One‐Pot Access to 2‐(Hetero)arylpyrrolidines.

et al. 2019

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2‐(Hetero)arylpyrrolidine fragment is found in a diverse array of biologically active molecules, both natural and unnatural. In recent years, a substantial increase in number of approved drugs featuring this scaffold is observed. Developing methods for the synthesis of such compounds has been essential for making progress in this field. Most of these methods require usage of metal catalysts and introduce additional chemical steps to obtain appropriately substituted starting compounds. This microreview details the one‐pot approach for the synthesis of pyrrolidine derivatives possessing (hetero)aromatic substituent at the second position of pyrrolidine ring based on usage of readily available N‐substituted 4,4‐diethoxybutan‐1‐amines and (hetero)aromatics as starting compounds and Bronsted acids as catalysts.

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Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Acid‐Catalyzed Cascade Reaction of 4‐Aminobutanal Derivatives with (Hetero)aromatic Nucleophiles: A Versatile One‐Pot Access to 2‐(Hetero)arylpyrrolidines.

et al. 2019

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“…Attempts to employ a triflic acid catalyst as described by Klumpp with coworkers for N ‐(4,4‐diethoxybutyl)ureas and aminoacetals also failed and no cyclization products were observed in the reaction mixtures. This may be attributed to the protonation of amidophosphoryl moiety by superacid, which lowers the nucleophilicity of the nitrogen atom and hinders the cyclization.…”

Section: Methodsmentioning

confidence: 99%

2‐(Het)aryl‐N‐phosphorylpyrrolidines via Cyclization of Phosphorus Acid Amides: A Regioselective Approach

et al. 2020

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A first successful synthesis of 2-(het)aryl-N-phosphorylpyrrolidines is reported starting from readily available N-(4,4-diethoxybutyl)amides of P(V) acids. A range of phenols and hydroxyl-substituted O-heterocycles may be employed into the reaction furnishing N-phosphorylated 2-(het)arylpyrrolidines with up to 90 % yield. The developed method permits a presence of sensitive to phosphorylation hydroxy groups and provides the easy and regioselective entry to target compounds. Pyrrolidine core is widespread in natural products [1,2] and synthetic drugs. [3] Phosphorus-containing pyrrolidine derivatives are of a special interest due to their various biological [4-8] and catalytic [9,10] properties. Among them, (pyrrolidin-1-yl) phosphoramidates are proposed for hepatitis C, [11] malaria and tuberculosis [12] treatment, possess anti-HIV [13-16] and antitumor [17,18] activity. Additionally, they employed as chiral ligands in various asymmetric reactions. Examples are metal-catalyzed stereoselective reduction of ketones, [19,20] ketimines [21] and alkenes, [22-24] various cycloadditions, [25-29] addition of boronic acids [30] and organotrifluoroborates [31] to alkenes, asymmetric ruthenium-catalyzed metallo-ene reaction [32] and Suzuki-Miyaura coupling. [33]

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“…The indolizidine ring system is thought to arise from a 6π-electrocyclization of intermediate 86 , followed by a deprotonation step. We also found the cyclization of urea substrates could provide access to nitrogen heterocycles by a reaction cascade [ 68 ]. Thus, urea 87 undergoes cyclization to provide compound 88 in excellent yield.…”

Section: Superelectrophilic Pericyclic Reactionsmentioning

confidence: 99%

Superelectrophiles: Recent Advances

Klumpp

Anokhin

2020

Molecules

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Cyclizations of N-carbamoyl and N-thiocarbamoyl iminium ions leading to ring-fused heterocycles

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Cited by 5 publications

References 15 publications

Acid‐Catalyzed Cascade Reaction of 4‐Aminobutanal Derivatives with (Hetero)aromatic Nucleophiles: A Versatile One‐Pot Access to 2‐(Hetero)arylpyrrolidines.

Acid‐Catalyzed Cascade Reaction of 4‐Aminobutanal Derivatives with (Hetero)aromatic Nucleophiles: A Versatile One‐Pot Access to 2‐(Hetero)arylpyrrolidines.

2‐(Het)aryl‐N‐phosphorylpyrrolidines via Cyclization of Phosphorus Acid Amides: A Regioselective Approach

Superelectrophiles: Recent Advances

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