Metal- and Oxidant-Free Green Three-Component Desulfurization and Deamination Condensation Approach to Fully Substituted 1<i>H</i>-1,2,4-Triazol-3-amines and Their Photophysical Properties

Guo, Wei; Liu, Gongping; Deng, Linhua; Mei, Weijie; Zou, Xiaoying; Zhong, Yumei; Zhuo, Xiaoya; Fan, Xiaolin; Zheng, Lvyin

doi:10.1021/acs.joc.1c02313

Cited by 25 publications

(10 citation statements)

References 66 publications

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“…Among them, many compounds with [1,2,4]triazolo pyridine core structures exhibit pharmacological and therapeutic effects, for example, as inhibitors of p38 for the treatment of chronic obstructive pulmonary disease, JAK2 inhibitors (CEP-33779) for anticancer therapy and GSK-3β inhibitors with potent neuroprotective effects . Owing to the attractive medical value of triazolo pyridines, their efficient synthesis and subsequent functionalization have attracted long-term attention. − One conventional approach for synthesizing [1,2,4]triazolo pyridines is through the tandem coupling/cyclization of 2-hydrazinopyridines with carboxylic acids. This reaction requires the addition of reagents such as POCl 3 /PCl 5 , iodobenzenediacetate (IBD), and 1,1′-carbonyldiimidazole (CDI) .…”

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confidence: 99%

Access to 3-Amino-[1,2,4]-triazolo Pyridines and Related Heterocycles via Electrochemically Induced Desulfurative Cyclization

Chen

Zou

et al. 2022

Org. Lett.

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An efficient, one-pot approach has been established for synthesizing a wide range of 3-amino-[1,2,4]-triazolo pyridines and related heterocycles from the electrochemically induced desulfurative cyclization of 2-hydrazinopyridines with isothiocyanates. The protocol allows for the formation of C−N bonds under simple conditions without transition metals or external oxidants. The practicability of this strategy is demonstrated by its broad substrate scope, good functional group compatibility, and gramscale synthesis. The late-stage modification of 3-amino-[1,2,4]triazolo pyridines enables us to obtain several molecules with potent anticancer activity.

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confidence: 99%

Access to 3-Amino-[1,2,4]-triazolo Pyridines and Related Heterocycles via Electrochemically Induced Desulfurative Cyclization

Chen

Zou

et al. 2022

Org. Lett.

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“…Kim and coworkers discovered an ortho -naphthoquinone-catalyzed aerobic oxidation of amines to aldehydes and ketones via the formation of a ketimine intermediate pathway . We also disclosed a base-promoted metal-/oxidant-free three-component tandem annulation for the synthesis of 2,4,5-trisubstituted thiazoles and 1 H -1,2,4-triazol-3-amines via C–N bond cleavage of amidines . Based on our previous report, we herein develop a facile and efficient 1,8-diazabicyclo[5.4.0]-undec-7-ene (DBU)-promoted deaminative thiolation reaction of 1 H -benzo[ d ]imidazol-2-amines and benzo[ d ]oxazol-2-amines using CS 2 as a convenient sulfur source without the requirement of any external catalysts, metals, and oxidants under room temperature (Scheme d).…”

Section: Introductionmentioning

confidence: 92%

DBU-Promoted Deaminative Thiolation of 1H-Benzo[d]imidazol-2-amines and Benzo[d]oxazol-2-amines

et al. 2022

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A facile and efficient catalyst-/metal-/oxidant-free DBU-promoted deaminative thiolation reaction of 1H-benzo[d]imidazol-2-amines and benzo[d]oxazol-2-amines has been developed at room temperature conditions in a one-pot protocol. This practical three-component strategy represents a novel and environmentally friendly reaction pathway toward the straightforward synthesis of various 2-thio-1H-benzo[d]imidazoles and 2thiobenzo[d]oxazoles using carbon disulfide as a sulfur source through C−N bond cleavage and C−S bond formation process. Different types of 1H-benzo[d]imidazol-2-amines, benzo[d]oxazol-2-amines, and organic bromides are suitable substrates. The gram-scale and late-stage modification experiments provide the potential applications based on this methodology in the field of organic and medicinal chemistry.

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“…Zheng and co‐workers reported a green MCR for the synthesis of fully substituted 1 H ‐1,2,4‐Triazol‐3‐amines 435 via desulfurization and deamination condensation of amidines 434 , isothiocyanates 221 and hydrazines 255 (Scheme 81). [99] The reaction is initiated by the nucleophilic attack of hydrazine on isothiocyanate to generate an intermediate 436 which readily isomerizes to intermediate 437 . This intermediate 437 reacts with amidine in presence of base to yield intermediate 438 .…”

Section: Five‐membered Heterocyclic Compoundsmentioning

confidence: 99%

Transition‐Metal‐Free Synthesis of N‐Heterocyclic Compounds via Multi‐Component Reactions

et al. 2023

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Multicomponent reactions (MCRs) have emerged as powerful tools in synthetic chemistry for the efficient synthesis of diverse molecular scaffolds, particularly nitrogen‐containing heterocycles. Despite their numerous advantages, the use of transition metal catalysts or additives in MCRs can present limitations due to cost, toxicity, and environmental concerns. In recent years, there has been a growing interest in transition metal‐free MCRs for the synthesis of N‐heterocyclic compounds. This review provides a comprehensive and concise overview of the recent advancements in transition metal‐free MCRs for the synthesis of valuable N‐heterocycles over the past five years. The review is systematically organized, categorizing the discussed MCRs based on the size of the heterocyclic ring and the number of nitrogen atoms. Only MCRs that result in the formation of heterocyclic rings containing at least one nitrogen atom are included, while the derivatization of N‐heterocycles using transition metal‐free MCRs falls outside the scope of this review. By highlighting the recent developments in this field, this review aims to showcase the potential and significance of transition metal‐free MCRs as sustainable and efficient strategies for accessing N‐heterocyclic compounds. The elimination of transition metals not only simplifies the reaction conditions but also contributes to greener and more environmentally friendly synthetic approaches. This review serves as a valuable resource for researchers interested in the design and application of transition metal‐free MCRs in the synthesis of nitrogen‐containing heterocycles.

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Metal- and Oxidant-Free Green Three-Component Desulfurization and Deamination Condensation Approach to Fully Substituted 1H-1,2,4-Triazol-3-amines and Their Photophysical Properties

Cited by 25 publications

References 66 publications

Access to 3-Amino-[1,2,4]-triazolo Pyridines and Related Heterocycles via Electrochemically Induced Desulfurative Cyclization

Access to 3-Amino-[1,2,4]-triazolo Pyridines and Related Heterocycles via Electrochemically Induced Desulfurative Cyclization

DBU-Promoted Deaminative Thiolation of 1H-Benzo[d]imidazol-2-amines and Benzo[d]oxazol-2-amines

Transition‐Metal‐Free Synthesis of N‐Heterocyclic Compounds via Multi‐Component Reactions

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