A One‐Step, Atom Economical Synthesis of Thieno[2,3‐<i>d</i>]pyrimidin‐4‐amine Derivatives by a Four‐Component Reaction

Shi, Taoda; Zerio, Christopher J.; Sivinski, Jared; Ambrose, Andrew J.; Moore, Kohlson T; Buckley, Thomas F.; Kaneko, Lynn K.; Zhang, Mae; Zhang, Donna D.; Chapman, Eli

doi:10.1002/ejoc.201900414

Cited by 10 publications

(5 citation statements)

References 31 publications

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“…Thieno[2,3-d]pyrimidin-4-amines 111 could be conveniently synthesized via four-component reactions of ketones 110 and malononitrile with elemental sulfur in formamide (Scheme 42). [41] The reaction was based on a first step of threecomponent Gewald reaction, which occurred at lower temperature, followed by cyclocondensation of the Gewald adduct 112 with formamide. The second step required high temperature up to 200°C and Na 2 HPO 4 as a catalyst.…”

Section: Thieno[23-d]pyrimidinementioning

confidence: 99%

Recent Advances in the Synthesis of Heterocycles via Reactions Involving Elemental Sulfur

Nguyen

2020

Adv Synth Catal

135

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Section: Thieno[23-d]pyrimidinementioning

confidence: 99%

Recent Advances in the Synthesis of Heterocycles via Reactions Involving Elemental Sulfur

Nguyen

2020

Adv Synth Catal

135

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“…The synthetic route to the new compound 3 is described in Scheme 1. When thieno-[2,3-d]pyrimidin-4-amine 1 [17] was allowed to react with aqueous formaldehyde in 1,4dioxane at 100 • C using a modified method [18], a new compound 2, N,N -bis(5,6,7,8tetrahydrobenzo [4,5]thieno [2,3-d]pyrimidin-4-yl)methanediamine, was formed in 75% yield. Subsequent cyclization of 2 with oxalyl chloride in the presence of pyridine in refluxing dichloroethane gave a new cyclic compound 3 in 66% yield.…”

Section: Resultsmentioning

confidence: 99%

1,3-Bis(5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-4-yl)imidazolidine-4,5-dione

Yin

Kim

Song

2022

Molbank

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A thieno[2,3-d]pyrimidine derivative 3 bearing a 4,5-imidazolidinedione moiety, 1,3-bis(5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-4-yl)imidazolidine-4,5-dione, was efficiently synthesized in 66% yield by the reaction of N,N′-bis(5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-4-yl)methanediamine 2 with oxalyl chloride in the presence of pyridine in refluxing dichloroethane for 10 h. The structure of the new synthesized compounds was fully characterized by 1H, 13C NMR, IR spectroscopy, mass-spectrometry and elemental analysis.

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“…They also reported another pyrimidine scaffolds 570 by reacting ketone 499 , malononitrile, S 8 and formamide at 200 °C in which Na 2 HPO 4 and triphenylphosphine are used as a catalyst and additive respectively (Scheme 110). [129] The efficacy of this process was demonstrated by the preparation of a multi‐targeted kinase inhibitor and an NRF2 pathway inhibitor with high atom‐ and step‐economy.…”

Section: Six‐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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A One‐Step, Atom Economical Synthesis of Thieno[2,3‐d]pyrimidin‐4‐amine Derivatives by a Four‐Component Reaction

Cited by 10 publications

References 31 publications

Recent Advances in the Synthesis of Heterocycles via Reactions Involving Elemental Sulfur

Recent Advances in the Synthesis of Heterocycles via Reactions Involving Elemental Sulfur

1,3-Bis(5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-4-yl)imidazolidine-4,5-dione

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

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