Imidates: an emerging synthon for N-heterocycles

Thakur, Rima; Jaiswal, Yogesh K.; Kumar, Amit

doi:10.1039/c9ob01899a

Cited by 38 publications

(21 citation statements)

References 59 publications

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“…Thus, they provide access to a wide range of structural motifs, including oxazolines, indazoles, and isoquinolines. 17 Acyclic N -sulfonyl imidates have been investigated as surrogates for azahetarenes in steroidal antiproliferative agents. 18 They have also been examined in drug discovery as prodrugs for esters and sulfonamides, addressing challenges associated with bioavailability and metabolism.…”

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confidence: 99%

“…Imidates are a synthetically versatile class of compounds that act as activated amide equivalents through their dual behavior as both electrophiles and nucleophiles. Thus, they provide access to a wide range of structural motifs, including oxazolines, indazoles, and isoquinolines . Acyclic N -sulfonyl imidates have been investigated as surrogates for azahetarenes in steroidal antiproliferative agents .…”

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confidence: 99%

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Cobalt-Catalyzed Cyclization of UnsaturatedN-Acyl Sulfonamides: a Diverted Mukaiyama Hydration Reaction

Fischer

Balkenhohl

Carreira

2022

JACS Au

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The cycloisomerization of β-, γ-, and δ-unsaturated N -acyl sulfonamides to N -sulfonyl lactams and imidates is reported. This transformation is effected in the presence of a Co III (salen) catalyst using t -BuOOH or air as the oxidant. The method shows good functional group tolerance (alkyl, aryl, heteroaryl, ether, N -Boc) and furnishes an underexplored class of cyclic building blocks. The strong solvent dependence of the transformation is investigated, and the synthetic versatility of the N -sulfonyl imidate product class is highlighted.

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confidence: 99%

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confidence: 99%

Cobalt-Catalyzed Cyclization of UnsaturatedN-Acyl Sulfonamides: a Diverted Mukaiyama Hydration Reaction

Fischer

Balkenhohl

Carreira

2022

JACS Au

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“…Recognizing their importance, Thakur et. al [11] and Fan et. al in the year 2019 [12] described the applications of imidates and amidines towards the synthesis of saturated and unsaturated heterocycles respectively.…”

Section: Introductionmentioning

confidence: 90%

Ortho‐Functionalization of Benzimidates and Benzamidines

2022

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In recent years, benzimidates and benzamidines have received tremendous importance as starting materials owing to their electronic properties and high reactivity. Their application as directing groups for constructing biologically active molecules has been a hot topic of discussion. Because of the presence of nucleophilic nitrogen in both these moieties, they can easily provide a co‐ordinating site to catalysts to form metallocyclic complexes which activate the inert Csp2−H bond thereby producing desired N‐heterocycles. In this review, we have summarized the developments in ortho‐functionalization of benzimidates and benzamidines using several coupling partners. Reaction mechanisms of protocols, their substrate versatility and limitations of those procedures along with their uses have also been addressed.

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“…The widespread interest in these privileged scaffolds has promoted extensive studies on their synthesis. The straightforward methods include the heterocyclization of amine with either carboxylic acids/derivatives (nitriles, orthoesters, and imidates) ( 20 , 21 ) or aldehyde ( 22 ). The other method is intramolecular oxidative cyclization of aniline Schiff base, which is often generated in situ from the condensation of amine and aldehyde.…”

Section: Introductionmentioning

confidence: 99%

Cooperative chemoenzymatic synthesis of N-heterocycles via synergizing bio- with organocatalysis

Tan

Zhang

et al. 2022

Sci. Adv.

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Inspired by Nature’s ingenuity, considerable progress has been made in recent years to develop chemoenzymatic processes by the integration of environmentally friendly feature of biocatalysis with versatile reactivity of chemocatalysis. However, the current types of chemoenzymatic processes are relatively few and mostly rely on metal catalysts. Here, we report a previously unexplored cooperative chemoenzymatic system for the synthesis of N-heterocycles. Starting from alcohols and amines, benzimidazole, pyrazine, quinazoline, indole, and quinoline can be obtained in excellent yields in water with O 2 as the terminal oxidant. Synthetic bridged flavin analog is served as a bifunctional organocatalyst for the regeneration of cofactor nicotinamide adenine dinucleotide in the bioprocess and oxidative cyclodehydrogenation in the chemoprocess. Compared to the classical acceptorless dehydrogenative coupling strategy, being metal and base free, requiring only water as solvent, and not needing atmosphere protection were observed for the present method, exhibiting a favorable green and sustainable alternative.

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Imidates: an emerging synthon for N-heterocycles

Abstract: This review highlights the recent application of imidates as building blocks for the synthesis of saturated and un-saturated N-heterocycles via C–N annulation reactions under acid/base/metal-catalyzed/radical-mediated reaction conditions.

Cited by 38 publications

References 59 publications

Cobalt-Catalyzed Cyclization of UnsaturatedN-Acyl Sulfonamides: a Diverted Mukaiyama Hydration Reaction

Cobalt-Catalyzed Cyclization of UnsaturatedN-Acyl Sulfonamides: a Diverted Mukaiyama Hydration Reaction

Ortho‐Functionalization of Benzimidates and Benzamidines

Cooperative chemoenzymatic synthesis of N-heterocycles via synergizing bio- with organocatalysis

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