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Search for "thiol" in Full Text gives 239 result(s) in Beilstein Journal of Organic Chemistry. Showing first 200.

Oxetanes: formation, reactivity and total syntheses of natural products

  • Peter Gabko,
  • Martin Kalník and
  • Maroš Bella

Beilstein J. Org. Chem. 2025, 21, 1324–1373, doi:10.3762/bjoc.21.101

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  • traced back to 3-oxetanone. In 2018, Bull and co-workers disclosed the first lithium-catalysed thiol alkylation using electron-rich 3-aryloxetan-3-ols 142 (Scheme 35) [84]. This protocol is completely chemoselective as no ring-opening was observed and the resulting oxetane sulphides 143 were obtained in
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Published 27 Jun 2025

Recent advances in oxidative radical difunctionalization of N-arylacrylamides enabled by carbon radical reagents

  • Jiangfei Chen,
  • Yi-Lin Qu,
  • Ming Yuan,
  • Xiang-Mei Wu,
  • Heng-Pei Jiang,
  • Ying Fu and
  • Shengrong Guo

Beilstein J. Org. Chem. 2025, 21, 1207–1271, doi:10.3762/bjoc.21.98

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Published 24 Jun 2025

Gold extraction at the molecular level using α- and β-cyclodextrins

  • Susana Santos Braga

Beilstein J. Org. Chem. 2025, 21, 1116–1125, doi:10.3762/bjoc.21.89

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  • to the thiol groups in the cyclodextrin. The authors further reported the process to be selective and to have good efficiency, with a gold removal yield as high as 96.1% in the presence of the thiolated β-CD derivative (Figure 5). Cyclodextrin recyclability was, however, not demonstrated and it is
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Published 06 Jun 2025

Recent advances in controllable/divergent synthesis

  • Jilei Cao,
  • Leiyang Bai and
  • Xuefeng Jiang

Beilstein J. Org. Chem. 2025, 21, 890–914, doi:10.3762/bjoc.21.73

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  • undergoes intramolecular cyclization into a proximal C(sp2)–H bond (ΔG‡ = +19.7 kcal·mol−1) to form Int-46, which reacts with 4-MePhSH (ΔG‡ = +14.9 kcal·mol−1) to yield radical intermediate Int-47 and a thiyl radical (4-MePhS·). Sequential thiol-assisted hydrogen shifts produce Int-48, followed by
  • barrierless thiyl radical addition and intersystem crossing (ISC) to furnish the final product. In contrast, acetonitrile’s polar aprotic environment destabilizes the carbene pathway, favoring direct reduction of the diazo moiety via electron transfer from the thiol. This solvent-gated selectivity underscores
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Published 07 May 2025

Recent advances in the electrochemical synthesis of organophosphorus compounds

  • Babak Kaboudin,
  • Milad Behroozi,
  • Sepideh Sadighi and
  • Fatemeh Asgharzadeh

Beilstein J. Org. Chem. 2025, 21, 770–797, doi:10.3762/bjoc.21.61

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  • oxidation of phosphines to phosphine oxides, followed by further anodic oxidation to give a phosphine oxide radical. In the subsequent step, treatment of the thiol radical (formed via the deprotonation of thiols with cesium carbonate and anodic oxidation) with the phosphine oxide radical gave the
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Published 16 Apr 2025

Orthogonal photoswitching of heterobivalent azobenzene glycoclusters: the effect of glycoligand orientation in bacterial adhesion

  • Leon M. Friedrich and
  • Thisbe K. Lindhorst

Beilstein J. Org. Chem. 2025, 21, 736–748, doi:10.3762/bjoc.21.57

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  • and excellent yield of 94% (Scheme 1). A chemoselective deprotection of the mannosyl thioacetate 7 to yield the glycosyl thiol 8 was achieved using 0.95 equivalents of sodium carbonate. The crude product was in turn submitted to a Buchwald–Hartwig–Migita cross-coupling reaction [33] with the
  • azobenzene derivative 9 [34] to furnish 10. This reaction had to be carried out at −78 °C in order to suppress nucleophilic substitution of the ortho-fluorine substituents in 9 by the thiol 8, a reaction that competes with the desired cross-coupling. For the second Buchwald–Hartwig–Migita cross-coupling, the
  • 3-O-(mannosyloxyazobenzene)-6-thio-mannoside 11 was employed, which was prepared according to a known procedure applied for the synthesis of the heterobivalent glycocluster 6βGlc3αMan 1 (cf. Supporting Information File 1, Scheme S1). The cross-coupling of thiol 11 with the azobenzene
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Published 08 Apr 2025

Photocatalyzed elaboration of antibody-based bioconjugates

  • Marine Le Stum,
  • Eugénie Romero and
  • Gary A. Molander

Beilstein J. Org. Chem. 2025, 21, 616–629, doi:10.3762/bjoc.21.49

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  • potential to overcome these limitations, particularly by enabling modifications under mild and controlled conditions. Unlike classical methods, such as thiol chemistry [22] or widely used click reactions [33], photocatalysis could provide innovative solutions to produce ADCs, especially in terms of
  • disulfide bridging sites in biomolecules to introduce specific functional groups (Figure 6) [44]. The bioconjugation reaction is based on thiol–yne coupling. Originally developed on peptides and proteins, this approach was applied to a fragment antigen-binding (Fab) antibody fragment (approximately 46 kDa
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Published 18 Mar 2025

Sequential two-step, one-pot microwave-assisted Urech synthesis of 5-monosubstituted hydantoins from L-amino acids in water

  • Wei-Jin Chang,
  • Sook Yee Liew,
  • Thomas Kurz and
  • Siow-Ping Tan

Beilstein J. Org. Chem. 2025, 21, 596–600, doi:10.3762/bjoc.21.46

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  • conversion of the thioether-containing methionine to hydantoin (H2j) was obtained with a moderate yield of 59%. Lastly, no hydantoin product was observed by 1H NMR when cysteine was subject to the one-pot procedure, possibly due to disulfide formation of the highly nucleophilic thiol group of the cysteine
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Published 14 Mar 2025

Photomechanochemistry: harnessing mechanical forces to enhance photochemical reactions

  • Francesco Mele,
  • Ana M. Constantin,
  • Andrea Porcheddu,
  • Raimondo Maggi,
  • Giovanni Maestri,
  • Nicola Della Ca’ and
  • Luca Capaldo

Beilstein J. Org. Chem. 2025, 21, 458–472, doi:10.3762/bjoc.21.33

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  • ). Overall, it was concluded that 7.1 and 7.2 first react to give 7.4 via a dark mechanochemical thiol–yne reaction; the latter is then converted to 7.3 by singlet oxygen generated in situ, by eosin Y. It is important to notice here that the reaction is proposed to proceed according to a different
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Published 03 Mar 2025

Visible-light-promoted radical cyclisation of unactivated alkenes in benzimidazoles: synthesis of difluoromethyl- and aryldifluoromethyl-substituted polycyclic imidazoles

  • Yujun Pang,
  • Jinglan Yan,
  • Nawaf Al-Maharik,
  • Qian Zhang,
  • Zeguo Fang and
  • Dong Li

Beilstein J. Org. Chem. 2025, 21, 234–241, doi:10.3762/bjoc.21.15

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  • difluoromethylene (PhCF2) group, stand out as particularly valuable in drug design. The CF2H group can serve as a lipophilic isostere for hydroxy (OH), amino (NH2), and thiol (SH) groups, thereby enhancing the efficacy and selectivity of therapeutic agents [4][5][6]. Similarly, the PhCF2 group offers unique
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Published 30 Jan 2025

Dioxazolones as electrophilic amide sources in copper-catalyzed and -mediated transformations

  • Seungmin Lee,
  • Minsuk Kim,
  • Hyewon Han and
  • Jongwoo Son

Beilstein J. Org. Chem. 2025, 21, 200–216, doi:10.3762/bjoc.21.12

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  • , a plausible reaction pathway is described in Figure 6. Decarboxylation of dioxazolone in INT-22 forms the copper nitrene intermediate INT-23. The thiol then attacks the electrophilic nitrogen center of INT-23, which further leads to the formation of intermediate INT-24. Finally, the desired product
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Published 22 Jan 2025

Quantifying the ability of the CF2H group as a hydrogen bond donor

  • Matthew E. Paolella,
  • Daniel S. Honeycutt,
  • Bradley M. Lipka,
  • Jacob M. Goldberg and
  • Fang Wang

Beilstein J. Org. Chem. 2025, 21, 189–199, doi:10.3762/bjoc.21.11

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  • ][10][11][12][13][14]. Of particular interest is the difluoromethyl group, CF2H, which exhibits hydrogen bond donating character due to the highly polarized F2C–H bond (Figure 1) [14][15][16][17][18][19][20][21][22][23][24]. This functional group is often used to mimic hydroxy or thiol groups but
  • that, although the CF2H group mimics hydroxy or thiol groups, it is a generally less effective hydrogen bond donor. Given that the HB donation ability of a particular functional group usually increases with increasing Brønsted acidity [49] we chose to incorporate the CF2H group into the backbone of N
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Published 20 Jan 2025

Synthesis of extended fluorinated tripeptides based on the tetrahydropyridazine scaffold

  • Thierry Milcent,
  • Pascal Retailleau,
  • Benoit Crousse and
  • Sandrine Ongeri

Beilstein J. Org. Chem. 2024, 20, 3174–3181, doi:10.3762/bjoc.20.262

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  • has become an essential structural motif in medicinal chemistry due to its hydrogen-bond donor capacity, its lipophilic character, and as a bioisostere for alcohol, thiol, or amine groups [16][17][18][19]. Thus, the contribution of fluorinated compounds to pharmaceuticals has been crucial for more
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Published 04 Dec 2024

Advances in the use of metal-free tetrapyrrolic macrocycles as catalysts

  • Mandeep K. Chahal

Beilstein J. Org. Chem. 2024, 20, 3085–3112, doi:10.3762/bjoc.20.257

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  • red light irradiation [97]. Firstly, they evaluated the photoreductant role of metal-free macrocycles, H2TPP (18) and PPIX 78, in the red light-induced C–H arylation of different substrates such as furan, coumarin, thiol, pivalamide, aryl thiaether and the selenium equivalents. Use of both macrocycles
  • transformations of biomolecules, such as thiol–yne reaction and decarboxylative alkynylation. The thiol–yne reaction of cyclohexanethiol (90) with phenylacetylene (89) in the presence of 1 mol % of H2TPP (18) under red LED irradiation provided the desired product 91 in up to 85% yield while the decarboxylative
  • in red light-induced C–X-bond formation on biologically relevant molecules 95–97, based on a thiol–yne reaction and decarboxylative alkynylation protocol (Figure 17d). Last year, Moyano and colleagues reported on amino-functionalized porphyrins as bifunctional organophotocatalysts, effectively
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Published 27 Nov 2024

Recent advances in transition-metal-free arylation reactions involving hypervalent iodine salts

  • Ritu Mamgain,
  • Kokila Sakthivel and
  • Fateh V. Singh

Beilstein J. Org. Chem. 2024, 20, 2891–2920, doi:10.3762/bjoc.20.243

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  • therapeutics, particularly in antibody–drug conjugates (ADCs). Cysteine (Cys) holds a special place in this context due to the distinctive nucleophilicity of its thiol side chain. The cysteine thiol group offers a reactive handle for site-selective modifications, allowing for the attachment of various
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Published 13 Nov 2024

A review of recent advances in electrochemical and photoelectrochemical late-stage functionalization classified by anodic oxidation, cathodic reduction, and paired electrolysis

  • Nian Li,
  • Ruzal Sitdikov,
  • Ajit Prabhakar Kale,
  • Joost Steverlynck,
  • Bo Li and
  • Magnus Rueping

Beilstein J. Org. Chem. 2024, 20, 2500–2566, doi:10.3762/bjoc.20.214

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  • method for the regioselective thiolation of aromatic C–H bonds by activating the thiol rather than the arene [19]. For their developed reaction, Pt electrodes were used in an undivided cell with a mixture of HFIP/DCE 3:1 at room temperature under argon. Late-stage functionalization was demonstrated for
  • leads to an intermediate product, which is then deprotonated, generating the thiol radical. This allowed for the preparation of the para-thiolation product (Scheme 11). Sulfonamides are an important class of bioactive molecules. In 2021, the Waldvogel group disclosed the first C(sp2)–H functionalization
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Published 09 Oct 2024

Facile preparation of fluorine-containing 2,3-epoxypropanoates and their epoxy ring-opening reactions with various nucleophiles

  • Yutaro Miyashita,
  • Sae Someya,
  • Tomoko Kawasaki-Takasuka,
  • Tomohiro Agou and
  • Takashi Yamazaki

Beilstein J. Org. Chem. 2024, 20, 2421–2433, doi:10.3762/bjoc.20.206

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  • ring-opening reaction with the same thiol (entries 6–8 in Table 3). It is interesting to note that a longer reaction time was required for these substrates which would be the major reason for the relatively low diastereomeric ratio (especially in the case of entry 8 in Table 3) while the CHF2
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Published 25 Sep 2024

Synthesis, electrochemical properties, and antioxidant activity of sterically hindered catechols with 1,3,4-oxadiazole, 1,2,4-triazole, thiazole or pyridine fragments

  • Daria A. Burmistrova,
  • Andrey Galustyan,
  • Nadezhda P. Pomortseva,
  • Kristina D. Pashaeva,
  • Maxim V. Arsenyev,
  • Oleg P. Demidov,
  • Mikhail A. Kiskin,
  • Andrey I. Poddel’sky,
  • Nadezhda T. Berberova and
  • Ivan V. Smolyaninov

Beilstein J. Org. Chem. 2024, 20, 2378–2391, doi:10.3762/bjoc.20.202

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  • corresponding thiols. The starting reagents such as substituted 1,3,4-oxadiazole-2-thiols and 4H-triazole-3-thiols are characterized by thiol–thione tautomerism, therefore their reactions with 3,5-di-tert-butyl-6-methoxymethylcatechol can proceed at the sulfur or nitrogen atom. In the case of mercapto
  • [25]. A feature of mercapto-substituted heterocycles is the possibility of their existence in two tautomeric forms: thiol or thione [26][27]. The ability to tautomeric transformations affects their biological activity and allows the use of these molecular blocks to design compounds with different
  • corresponding thiol [35][36][37][38], in the nucleophilic substitution reaction in the aromatic ring of catechol [39][40] or under electrochemical conditions [41][42][43]. An anodic activation of catechols in the presence of a thiol leads to S-functionalized catechols with triazole, triazine, pyrimidine
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Published 19 Sep 2024

Improved deconvolution of natural products’ protein targets using diagnostic ions from chemical proteomics linkers

  • Andreas Wiest and
  • Pavel Kielkowski

Beilstein J. Org. Chem. 2024, 20, 2323–2341, doi:10.3762/bjoc.20.199

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  • interrupted CuAAC mechanism [65]. The thiotriazole product of this reaction, which is indistinguishable in the protein-level downstream analysis, is formed by coupling between protein free thiol groups and the triazole–copper adduct (Figure 4). However, its formation can be avoided by eliminating the free
  • , in this case, the cysteine thiols were derivatized and the cysteine C–S bond was previously described to be susceptible to fragmentation, the fragments containing the thiol provide the information on the structure of the modified amino acid side chain [107][108]. Although the study was focused on the
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Published 12 Sep 2024

Stereoselective mechanochemical synthesis of thiomalonate Michael adducts via iminium catalysis by chiral primary amines

  • Michał Błauciak,
  • Dominika Andrzejczyk,
  • Błażej Dziuk and
  • Rafał Kowalczyk

Beilstein J. Org. Chem. 2024, 20, 2313–2322, doi:10.3762/bjoc.20.198

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  • guanidine motif in AA-3 compared to simple AA-1. Alterations in the thiol structure within thiomalonates significantly impact their stability and reactivity, thereby influencing both reaction efficiency and stereochemical outcome, as demonstrated in the case of catalysis employing bifunctional hydrogen bond
  • adduct. Hence, after 24 hours up to 9% of sulfa-adduct was formed (see Supporting Information File 1 for details). Unfavorable in this case is the formation of ketene via thiol elimination [40], leading to the formation of a mixture of products where the thia-Michael adduct predominates over the desired
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Published 12 Sep 2024

Catalysing (organo-)catalysis: Trends in the application of machine learning to enantioselective organocatalysis

  • Stefan P. Schmid,
  • Leon Schlosser,
  • Frank Glorius and
  • Kjell Jorner

Beilstein J. Org. Chem. 2024, 20, 2280–2304, doi:10.3762/bjoc.20.196

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Published 10 Sep 2024

Selective hydrolysis of α-oxo ketene N,S-acetals in water: switchable aqueous synthesis of β-keto thioesters and β-keto amides

  • Haifeng Yu,
  • Wanting Zhang,
  • Xuejing Cui,
  • Zida Liu,
  • Xifu Zhang and
  • Xiaobo Zhao

Beilstein J. Org. Chem. 2024, 20, 2225–2233, doi:10.3762/bjoc.20.190

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  • ][62][63][64], we conducted research on their organic reactions in water and reported some good results, such as thioacetalization using ketene dithioacetals as odorless thiol equivalent [65], Friedel–Crafts alkylation of cyclic ketene dithioacetals with alcohols [66], the hydrolysis of chain α-oxo
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Published 03 Sep 2024

Efficacy of radical reactions of isocyanides with heteroatom radicals in organic synthesis

  • Akiya Ogawa and
  • Yuki Yamamoto

Beilstein J. Org. Chem. 2024, 20, 2114–2128, doi:10.3762/bjoc.20.182

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  • a pioneering study, Ito and Saegusa et al. reported the radical addition of thiols to isocyanides (Scheme 2) [27]. Thermal decomposition of AIBN as a radical initiator generates the 2-cyano-2-propyl radical ((NC)(CH3)2C•), which abstracts hydrogen from the thiol (R’SH) to form the thiyl radical (R’S
  • •). The formed R’S• adds to isocyanide (RNC) to generate imidoyl radical intermediate 2 (E = R’S), which abstracts hydrogen from thiol to give the corresponding thioformimidate 3 (E = R’S) with regeneration of R’S•. Thus, the hydrothiolation of isocyanides with thiols proceeds by the radical chain
  • by ESR measurement [37]. Similar to the thiol addition to isocyanides, disubstituted phosphines (R’2PH) induce radical addition to isocyanides in the presence of AIBN as a radical initiator yielding the corresponding iminoformyl phosphines, R’2P–CH=NR, (12, R = c-C6H11 or n-C6H11, E = Et2P) in good
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Published 26 Aug 2024

Multicomponent syntheses of pyrazoles via (3 + 2)-cyclocondensation and (3 + 2)-cycloaddition key steps

  • Ignaz Betcke,
  • Alissa C. Götzinger,
  • Maryna M. Kornet and
  • Thomas J. J. Müller

Beilstein J. Org. Chem. 2024, 20, 2024–2077, doi:10.3762/bjoc.20.178

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  • 47, can be accessed from polyfunctional hydrazine derivatives via multicomponent reactions. For the preparation of pyrazoles 47, 4-amino-5-hydrazinyl-4H-1,2,4-triazole-3-thiol (44), phenylacyl bromides 45, and benzoylacetonitriles 46 were chosen as starting materials (Scheme 13) [67]. Thereby
  • , benzoylacetonitrile and the hydrazinyl moiety constitute the pyrazole nucleus, while phenylacyl bromide condenses with the thiol and amino groups to form the thiadiazinyl moiety. In addition to bromoacetylchromenone, phenylacetyl bromide can also be used as an alternative starting material. 1,3-Dielectrophilic β
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Published 16 Aug 2024

A new platform for the synthesis of diketopyrrolopyrrole derivatives via nucleophilic aromatic substitution reactions

  • Vitor A. S. Almodovar and
  • Augusto C. Tomé

Beilstein J. Org. Chem. 2024, 20, 1933–1939, doi:10.3762/bjoc.20.169

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  • aromatic substitution; phenol; thiol; Introduction Diketopyrrolopyrroles (DPPs) are a class of organic pigments discovered by serendipity in the 1970s [1][2]. Generally, N-unsubstituted DPP derivatives exhibit high melting points, low solubility in most solvents, and strong absorption in the visible
  • excellent nucleophiles and generally react under mild conditions, resulting in the substitution of the 4-F atom of the pentafluorophenyl groups. In this case, reactions with thiols were performed in dry DMF and K2CO3 was used as the base. Three different thiols were tested: pyridine-4-thiol, pyridine-2
  • -thiol and 4-(acetylamino)benzenethiol. The reaction with pyridine-4-thiol yielded a mixture of the di- and monosubstituted compounds 3a and 4a in 51% and 23% yields, respectively. Conversely, for the reaction with pyridine-2-thiol, exclusively produced the disubstituted compound 3b in an 85% yield
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Published 08 Aug 2024
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