The effect of neighbouring group participation and possible long range remote group participation in O-glycosylation

• Rituparna Das and
• Balaram Mukhopadhyay

Beilstein J. Org. Chem. 2025, 21, 369–406, doi:10.3762/bjoc.21.27

• the extremes of SN1 and SN2 pathway by employing the effect of counter ions, showing close resemblance with the SNi mechanism [41], conforming to the famous Winstein’s ion-pair theory [42] and draws analogy with chlorination of alcohols by thionyl chloride [43]. Incorporating the role of counter ion

Synthesis, characterization, antimicrobial, cytotoxic and carbonic anhydrase inhibition activities of multifunctional pyrazolo-1,2-benzothiazine acetamides

• Ayesha Saeed,
• Shahana Ehsan,
• Muhammad Zia-ur-Rehman,
• Erin M. Marshall,
• Sandra Loesgen,
• Abdus Saleem,
• Simone Giovannuzzi and
• Claudiu T. Supuran

Beilstein J. Org. Chem. 2025, 21, 348–357, doi:10.3762/bjoc.21.25

• complex as the amide coupling agent with thionyl chloride [38] (Figure 1C). Recently, benzothiazine scaffolds of phenyl acetamides were synthesized as potent inhibitors for ureolytic infections [39] (Figure 1D). Saccharine (a sweetener) was reported to be a potent carbonic anhydrase inhibitor (CAI) by

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

• condensation of carboxylic acids with anilines, often promoted by activating agents such as thionyl chloride or peptide coupling agents [86][87][88][89]. However, these protocols rely on environmentally harmful reagents and produce unwanted byproduct wastes. Recently, the research group of Son showcased a

Intramolecular C–H arylation of pyridine derivatives with a palladium catalyst for the synthesis of multiply fused heteroaromatic compounds

• Yuki Nakanishi,
• Shoichi Sugita,
• Kentaro Okano and
• Atsunori Mori

Beilstein J. Org. Chem. 2024, 20, 3256–3262, doi:10.3762/bjoc.20.269

• reaction of the corresponding heteroaromatic carboxylic acids with thionyl chloride followed by treatment with N-octyl-2-bromoaniline [15]. The reactions proceeded smoothly affording products 1a–c in good yields as shown in Scheme 1. We then studied the reaction of quinoline amide 1a under several

Synthesis of 2H-azirine-2,2-dicarboxylic acids and their derivatives

• Anastasiya V. Agafonova,
• Mikhail S. Novikov and
• Alexander F. Khlebnikov

Beilstein J. Org. Chem. 2024, 20, 3191–3197, doi:10.3762/bjoc.20.264

• included oxidation of aldehydes 4 with Oxone to acids 5 and the conversion of the latter into acid chlorides with thionyl chloride. The first reaction sequence was suitable for obtaining compounds 1a–c,e,f with substituents tolerant to radical reaction conditions. A significant advantage of the method is

• the conversion of the latter to the acid chlorides 1 with thionyl chloride proceeded with yields of 77–92%. This made it possible to synthesize the target isoxazoles 1b,d,g–j with fairly high yields. Having in hand a set of isoxazoles 1a–i containing aryl substituents at the 3-position of the

A facile three-component route to powerful 5-aryldeazaalloxazine photocatalysts

• Ivana Weisheitelová,
• Radek Cibulka,
• Marek Sikorski and
• Tetiana Pavlovska

Beilstein J. Org. Chem. 2024, 20, 1831–1838, doi:10.3762/bjoc.20.161

• (1H,3H)-dione) by refluxing with thionyl chloride [20][23]. However, the preparation of partially hydrogenated 5,10-dihydropyrimido[4,5-b]quinolinediones has been repeatedly reported by one-pot condensation of substituted anilines, aldehydes and barbituric acids, usually in protic solvents (alcohols

Syntheses and medicinal chemistry of spiro heterocyclic steroids

• Laura L. Romero-Hernández,
• Ana Isabel Ahuja-Casarín,
• Penélope Merino-Montiel,
• Sara Montiel-Smith,
• José Luis Vega-Báez and
• Jesús Sandoval-Ramírez

Beilstein J. Org. Chem. 2024, 20, 1713–1745, doi:10.3762/bjoc.20.152

• ester under basic conditions was carried out, followed by the transformation of the carboxyl group to the amides 165 and 166 by treatment with thionyl chloride and the corresponding amine. Tetraoxanes were obtained from ketones 163, 165, and 166 by a peroxyacylation reaction using an acidic hydrogen

Skeletal rearrangement of 6,8-dioxabicyclo[3.2.1]octan-4-ols promoted by thionyl chloride or Appel conditions

• Martyn Jevric,
• Julian Klepp,
• Johannes Puschnig,
• Oscar Lamb,
• Christopher J. Sumby and
• Ben W. Greatrex

Beilstein J. Org. Chem. 2024, 20, 823–829, doi:10.3762/bjoc.20.74

• the alkoxytriphenylphosphonium intermediate. Several reactions of the products were investigated to show the utility of the rearrangement. Keywords: bicyclic ring; cyrene; levoglucosenone; rearrangement; thionyl chloride; Introduction The 6,8-dioxabicyclo[3.2.1]octane derivative levoglucosenone (1

Synthesis of π-conjugated polycyclic compounds by late-stage extrusion of chalcogen fragments

• Aissam Okba,
• Pablo Simón Marqués,
• Kyohei Matsuo,
• Naoki Aratani,
• Hiroko Yamada,
• Gwénaël Rapenne and
• Claire Kammerer

Beilstein J. Org. Chem. 2024, 20, 287–305, doi:10.3762/bjoc.20.30

• 6-membered rings containing a sulfoxide moiety. For instance, Grainger and co-workers designed a series of naphthotrithiin-2-oxides, such as 47, to act as SO transfer reagents (Scheme 13) [79]. These triplet SO precursors were prepared by treatment of 1,8-naphthalene dithiols with thionyl chloride

A novel recyclable organocatalyst for the gram-scale enantioselective synthesis of (S)-baclofen

• Gyula Dargó,
• Dóra Erdélyi,
• Balázs Molnár,
• Péter Kisszékelyi,
• Zsófia Garádi and
• József Kupai

Beilstein J. Org. Chem. 2023, 19, 1811–1824, doi:10.3762/bjoc.19.133

• corresponding acyl chloride 11 with thionyl chloride. Finally, the cinchona squaramide with linker 7 and the octadecylated gallic acid chloride 11 were coupled to form an amide using triethylamine as a base. The crude product was purified by chromatography and precipitated from acetonitrile to gain the

Synthetic strategies for the preparation of γ-phostams: 1,2-azaphospholidine 2-oxides and 1,2-azaphospholine 2-oxides

• Jiaxi Xu

Beilstein J. Org. Chem. 2022, 18, 889–915, doi:10.3762/bjoc.18.90

• -amino-4-(hydroxy(methyl)phosphoryl)butanoic acid (68) by treatment with phosphorus pentachloride or thionyl chloride, respectively, in the presence of triethylamine when he synthesized phosphonopeptides. Similar yields were obtained for these two different chlorinating reagents. Ethyl 2-methyl-1,2

• -(diethoxyphosphoryl)benzoic acid (198) and amine derivatives. They first converted 2-(diethoxyphosphoryl)benzoic acid (198) into its anhydride 1-ethoxy-3H-benzo[c][1,2]oxaphosphol-3-one 1-oxide (199) by treatment with thionyl chloride under nitrogen. The mixed anhydride 199 was further treated with phosphorus

First series of N-alkylamino peptoid homooligomers: solution phase synthesis and conformational investigation

• Maxime Pypec,
• Laurent Jouffret,
• Claude Taillefumier and
• Olivier Roy

Beilstein J. Org. Chem. 2022, 18, 845–854, doi:10.3762/bjoc.18.85

• 1c, respectively (Scheme 2). The N-Fmoc-protected acid partner 1c was readily prepared from 1a under standard conditions. After a few unsuccessful attempts of coupling using the azabenzotriazole-based coupling reagent HATU [42] or via the formation of an acid chloride with thionyl chloride, we turned

Efficient synthesis of ethyl 2-(oxazolin-2-yl)alkanoates via ethoxycarbonylketene-induced electrophilic ring expansion of aziridines

• Yelong Lei and
• Jiaxi Xu

Beilstein J. Org. Chem. 2022, 18, 70–76, doi:10.3762/bjoc.18.6

• diastereomeric products 3 were obtained. Compared with previously reported methods, our current method is more convenient and low cost without any activators (such as thionyl chloride, sulfonyl chlorides, NBS, electrophiles, and radical initiators) and catalysts. The current synthetic strategy is a clean

Synthetic strategies toward 1,3-oxathiolane nucleoside analogues

• Umesh P. Aher,
• Dhananjai Srivastava,
• Girij P. Singh and
• Jayashree B. S

Beilstein J. Org. Chem. 2021, 17, 2680–2715, doi:10.3762/bjoc.17.182

• -Hydroxyoxathiolane intermediate 56a was isolated in a DKR procedure by Whitehead and co-workers (Scheme 38) [55]. Further, 5-chlorooxathiolane 56 was isolated from chlorination reaction of 5-hydroxyoxathiolane 56a using thionyl chloride in presence of catalytic DMF and dichloromethane solvent. This further reacted

Double-headed nucleosides: Synthesis and applications

• Vineet Verma,
• Jyotirmoy Maity,
• Vipin K. Maikhuri,
• Ritika Sharma,
• Himal K. Ganguly and
• Ashok K. Prasad

Beilstein J. Org. Chem. 2021, 17, 1392–1439, doi:10.3762/bjoc.17.98

• using thionyl chloride in dichloromethane, followed by the treatment of the product with N3-benzoylthymine under basic conditions (K2CO3 in DMF) to produce the nucleoside 18. The removal of the tert-butyldimethylsilyl group from nucleoside 18, followed by dimethoxytritylation at the primary hydroxy and

N-tert-Butanesulfinyl imines in the asymmetric synthesis of nitrogen-containing heterocycles

• Joseane A. Mendes,
• Paulo R. R. Costa,
• Miguel Yus,
• Francisco Foubelo and
• Camilla D. Buarque

Beilstein J. Org. Chem. 2021, 17, 1096–1140, doi:10.3762/bjoc.17.86

• , because of the influence of the bulky tert-butyl in the most stable conformation of the sulfinyl imine (Scheme 30). The authors also demonstrated the synthetic utility of compounds 100. Their reaction with thionyl chloride in methanol produced removal of the sulfinyl group and formation of the

Stereoselective syntheses of 3-aminocyclooctanetriols and halocyclooctanetriols

• Emine Salamci and
• Yunus Zozik

Beilstein J. Org. Chem. 2021, 17, 705–710, doi:10.3762/bjoc.17.59

• oxidation of the double bond gave diacetatediol 7 [33]. Treatment of diacetatediol 7 with thionyl chloride in pyridine gave the corresponding cyclic sulfite 8 in 95% yield (Scheme 1). Oxidation of the cyclic sulfite 8 with sodium periodate in the presence of ruthenium trichloride provided the corresponding

Synthetic strategies of phosphonodepsipeptides

• Jiaxi Xu

Beilstein J. Org. Chem. 2021, 17, 461–484, doi:10.3762/bjoc.17.41

• ) were modest inhibitors. The synthesis started from diphenyl N-Cbz-1-aminoalkylphosphonates 11 (Scheme 1). They were transformed to dimethyl esters via transesterification and further to monomethyl esters 12 via basic hydrolysis. After chlorination with thionyl chloride, the monomethyl esters 12 were

• carboxypeptidase A. Synthesis of α-phosphonodepsidipeptides containing enantiopure hydroxy ester as VanX inhibitors. Synthesis of α-phosphonodepsidipeptides as VanX inhibitors. Synthesis of optically active α-phosphonodepsidipeptides as VanX inhibitors. The synthesis of phosphonodepsipeptides through a thionyl

• chloride-catalyzed esterification of N-Cbz aminoalkylphosphonic acids 32 and 4-nitrobenyl 2-hydroxyalkanoates 33. Synthesis of α-phosphinodipeptidamide as a hapten. Synthesis of α-phosphonodepsioctapeptide 41. Synthesis of phosphonodepsipeptides via an in situ-generated phosphonochloridate. Synthesis of α

Supramolecular polymers with reversed viscosity/temperature profile for application in motor oils

• Jan-Erik Ostwaldt,
• Christoph Hirschhäuser,
• Stefan K. Maier,
• Carsten Schmuck and
• Jochen Niemeyer

Beilstein J. Org. Chem. 2021, 17, 105–114, doi:10.3762/bjoc.17.11

• cyclisation. Thus, all compounds feature a central BINAM unit, which is connected to the BUs (GCP or ACP) via a propionamide linker [29]. The synthesis of compound 1 was carried out starting from BINAM by coupling with GCP derivate 5 [12][13] after activation with thionyl chloride (see Figure 3). Deprotection

Hierarchically assembled helicates as reaction platform – from stoichiometric Diels–Alder reactions to enamine catalysis

• David Van Craen,
• Jenny Begall,
• Johannes Großkurth,
• Leonard Himmel,
• Oliver Linnenberg,
• Elisabeth Isaak and
• Markus Albrecht

Beilstein J. Org. Chem. 2020, 16, 2338–2345, doi:10.3762/bjoc.16.195

• the amino alcohols 10a–d were protected with a Boc group [42][43]. Esterification of the protected alcohols 11a–d [33][44] with 2,3-dioxosulfinylbenzoyl chloride obtained from 2,3-dihydroxybenzoic acid and thionyl chloride afforded the N-Boc-substituted catechol ligands 12a–d [33][36]. They were

Fluorinated phenylalanines: synthesis and pharmaceutical applications

• Laila F. Awad and
• Mohammed Salah Ayoup

Beilstein J. Org. Chem. 2020, 16, 1022–1050, doi:10.3762/bjoc.16.91

• synthesis from ethyl trifluoropyruvate hemiketal The reaction of ethyl trifluoropyruvate hemiketal 130 with thionyl chloride in pyridine afforded the chlorinated derivative 131, which upon treatment with zinc powder in DMF, afforded the dihalogenated olefin 132. The substitution of one fluorine atom in 132

Pd-catalyzed asymmetric Suzuki–Miyaura coupling reactions for the synthesis of chiral biaryl compounds with a large steric substituent at the 2-position

• Yongsu Li,
• Bendu Pan,
• Xuefeng He,
• Wang Xia,
• Yaqi Zhang,
• Hao Liang,
• Chitreddy V. Subba Reddy,
• Rihui Cao and
• Liqin Qiu

Beilstein J. Org. Chem. 2020, 16, 966–973, doi:10.3762/bjoc.16.85

• : A round bottom flask (100 mL) was charged with 2-bromo-3-methylbenzoic acid (2.0 g, 1.0 equiv) and SOCl2 (16 mL) was added at room temperature. Then, the reaction mixture was refluxed at 80 °C for 2 h. After completion of the reaction, the excess thionyl chloride was removed by evaporation using a

A systematic review on silica-, carbon-, and magnetic materials-supported copper species as efficient heterogeneous nanocatalysts in “click” reactions

• Pezhman Shiri and
• Jasem Aboonajmi

Beilstein J. Org. Chem. 2020, 16, 551–586, doi:10.3762/bjoc.16.52

• ” products by this new catalyst was successfully accomplished. To synthesize the catalyst, first, GO–COCl was created by the reaction of GO with thionyl chloride in DMF at reflux for 24 h. Then, the resulting GO–COCl compound was treated with 1,7-diaminoheptane to afford amino-modified graphene oxide (GO–CO–NH2

Chemical tuning of photoswitchable azobenzenes: a photopharmacological case study using nicotinic transmission

• Lorenzo Sansalone,
• Jun Zhao,
• Matthew T. Richers and
• Graham C. R. Ellis-Davies

Beilstein J. Org. Chem. 2019, 15, 2812–2821, doi:10.3762/bjoc.15.274

• maleimide using hydroxymethylation with formaldehyde, followed by treatment with thionyl chloride to give a chloromethyl intermediate, which was reacted in situ with maleimide to give 1 in 6% overall yield. Crucially, photochrome 1 also maintained the near-ideal photochemical properties of Hecht’s 4FABs [12

A review of asymmetric synthetic organic electrochemistry and electrocatalysis: concepts, applications, recent developments and future directions

• Munmun Ghosh,
• Valmik S. Shinde and
• Magnus Rueping

Beilstein J. Org. Chem. 2019, 15, 2710–2746, doi:10.3762/bjoc.15.264

• with thionyl chloride followed by derivatization with (S)-(−)-phenylalanine methyl ester. The applicability of this modified electrode [(S)-CelPheM] was tested by using it as a cathode for the electrochemical reduction of 4-acetylpyridine (1). GC analysis of the product indicated the formation of the