C2 to C6 biobased carbonyl platforms for fine chemistry

• Jingjing Jiang,
• Muhammad Noman Haider Tariq,
• Florence Popowycz,
• Yanlong Gu and
• Yves Queneau

Beilstein J. Org. Chem. 2025, 21, 2103–2172, doi:10.3762/bjoc.21.165

Research progress on calixarene/pillararene-based controlled drug release systems

• Liu-Huan Yi,
• Jian Qin,
• Si-Ran Lu,
• Liu-Pan Yang,
• Li-Li Wang and
• Huan Yao

Beilstein J. Org. Chem. 2025, 21, 1757–1785, doi:10.3762/bjoc.21.139

• chiral CA named chiral azo-calix[4]arene derivative (FC4AD) (Figure 10) [117]. Its interaction with enantiomers of aminoindanol in solution was investigated. It was found that FC4AD has high selective binding and release for (1R,2S)-1-amino-2-indanol, forming a 1:1 complex. S-phenethylamine was used as a

Investigations of amination reactions on an antimalarial 1,2,4-triazolo[4,3-a]pyrazine scaffold

• Henry S. T. Smith,
• Ben Giuliani,
• Kanchana Wijesekera,
• Kah Yean Lum,
• Sandra Duffy,
• Aaron Lock,
• Jonathan M. White,
• Vicky M. Avery and
• Rohan A. Davis

Beilstein J. Org. Chem. 2025, 21, 1126–1134, doi:10.3762/bjoc.21.90

• et al. for 5-position halogenated scaffolds [10]. Several different triazolopyrazine compounds bearing chlorine, bromine or iodine at the 5-position, gave no ipso-substituted (5-substituted) products when refluxed in toluene with phenethylamine, with all major products being substituted at the 8

• ]triazolo[4,3-a]pyrazine (compound 1; Scheme 1) according to the approach previously described by Korsik et al. [10] was performed, but without reflux, in order to compare the yield obtained for the aminated product under our further modified conditions (neat phenethylamine only, room temperature; Scheme 1

• column chromatography (and additionally by HPLC for the toluene reaction), the reactions also gave comparable yields of compound 2 (70% for toluene/silica and 82% for only phenethylamine at room temperature). Only the tele-substituted product was observed in either reaction mixture, consistent with

Facile one-pot reduction of β-nitrostyrenes to phenethylamines using sodium borohydride and copper(II) chloride

• Laura D’Andrea and
• Simon Jademyr

Beilstein J. Org. Chem. 2025, 21, 39–46, doi:10.3762/bjoc.21.4

• ; phenethylamine; Introduction The phenethylamine scaffold represents a recurring motif among natural and synthetic drug molecules. The latter are mainly constituted by a varied class of substituted phenylethylamines exhibiting psychoactive properties, and typically employed for medical and recreational use [1][2

• limited, since a NaBH4/transition metal salt system is mostly used to reduce nitroarenes [23][24][25][26]. One of the reported methods takes advantage of titanium(IV) isopropoxide as a catalyst to prepare varied β-phenethylamine analogues. Despite its simplicity, the reaction time is quite prolonged (from

• crucial role in the synthesis of phenethylamine analogues via this method. Dithering before the addition of the copper solution leads to the formation of Micheal adducts, which decrease the product yields. This phenomenon is due to the nature of β-nitrostyrenes, displaying considerable delocalization

5th International Symposium on Synthesis and Catalysis (ISySyCat2023)

• Anthony J. Burke and
• Elisabete P. Carreiro

Beilstein J. Org. Chem. 2024, 20, 2704–2707, doi:10.3762/bjoc.20.227

• reported that imidazole analogs behaved differently due to the ʟ-histidine unit representing a nonphenyl scaffold. Some important data on the bioisosteric modifications of 2-phenethylamine derivatives, focusing on their affinity and core aromatic diversity, were included. In another Review article

2-Heteroarylethylamines in medicinal chemistry: a review of 2-phenethylamine satellite chemical space

• Carlos Nieto,
• Alejandro Manchado,
• Ángel García-González,
• David Díez and
• Narciso M. Garrido

Beilstein J. Org. Chem. 2024, 20, 1880–1893, doi:10.3762/bjoc.20.163

• area of chemical space of biological importance) in medicinal chemistry is the 2-phenethyl moiety, a key component of diverse drug-like entities. Although the core 2-phenethylamine structure has been recognized by the drug discovery community, little attention has been given to the various ring-based

• examples, which will be a valuable repository of phenyl, heteroaryl, and other replacement units of high value to the drug discovery community. Keywords: bioisosteres; 2-heteroarylethylamines; medicinal chemistry; 2-phenethylamine; scaffold hopping; Introduction One of the major hit-2-lead exploration

• affinity to key phenethylamine targets like adrenergic or histamine-type receptors, but also to novel ones such as TAAR1 (trace-amine-associated receptor 1), σ1/2 (sigma receptors 1 and 2), or AChE (acetylcholinesterase). Similar to our previous review, a descriptive, simple scope is presented below to

Synthesis and biological evaluation of Argemone mexicana-inspired antimicrobials

• Jessica Villegas,
• Bryce C. Ball,
• Katelyn M. Shouse,
• Caleb W. VanArragon,
• Ashley N. Wasserman,
• Hannah E. Bhakta,
• Allen G. Oliver,
• Danielle A. Orozco-Nunnelly and
• Jeffrey M. Pruet

Beilstein J. Org. Chem. 2023, 19, 1511–1524, doi:10.3762/bjoc.19.108

• generated via reductive amination of a substituted benzaldehyde and a substituted phenethylamine [30]. Thus, a variety of substituted berberine variants were rapidly generated as shown in Scheme 2. Our first variant (B1) resulted from the reductive amination of m-anisaldehyde with 3-methoxyphenethylamine

Eschenmoser coupling reactions starting from primary thioamides. When do they work and when not?

• Lukáš Marek,
• Jiří Váňa,
• Jan Svoboda and
• Jiří Hanusek

Beilstein J. Org. Chem. 2023, 19, 808–819, doi:10.3762/bjoc.19.61

• group. The leaving abilities of "aniline" nitrogen (anilinium has a pKa = 4.60 in water) [22] in intermediate 16 (Scheme 7) and "phenethylamine" nitrogen (2-phenyl-2-propylammonium has a pKa = 10.38 in water) [34] in 7a (Scheme 3) must differ by several orders of magnitude, which makes the irreversible

• , then the Hantzsch cyclization pathway can occur, and the structure of the product depends on the leaving ability of the lactam/amide nitrogen. A good leaving “aniline” group prefers C–N cleavage, whereas the worse leaving “phenethylamine” prefers water elimination. Experimental The starting 1,1

1,2-Naphthoquinone-4-sulfonic acid salts in organic synthesis

• Ruan Carlos B. Ribeiro,
• Patricia G. Ferreira,
• Amanda de A. Borges,
• Luana da S. M. Forezi,
• Fernando de Carvalho da Silva and
• Vitor F. Ferreira

Beilstein J. Org. Chem. 2022, 18, 53–69, doi:10.3762/bjoc.18.5

• phenethylamine derivatives (amphetamine, methamphetamine, 2,5-dimethoxy-4-methylamphetamine, mescaline, ephedrine, and norephedrine). The reaction products were separated by thin-layer chromatography and analyzed by elemental analysis, nuclear magnetic resonance, infrared spectroscopy, and mass spectrometry. In

Isolation and characterization of new phenolic siderophores with antimicrobial properties from Pseudomonas sp. UIAU-6B

• Emmanuel T. Oluwabusola,
• Olusoji O. Adebisi,
• Fernando Reyes,
• Kojo S. Acquah,
• Mercedes De La Cruz,
• Larry L. Mweetwa,
• Joy E. Rajakulendran,
• Digby F. Warner,
• Deng Hai,
• Rainer Ebel and
• Marcel Jaspars

Beilstein J. Org. Chem. 2021, 17, 2390–2398, doi:10.3762/bjoc.17.156

• through deviation of the salimethyloxazolinyl-thioester intermediate 8 from the assembly line via an unusually facile C–N-bond opening of the ring to generate an ester bond, and followed directly by amination (+ NH3), the addition of histamine and phenethylamine units to form compounds 1, 2, and 3

• , respectively (Figure 3). Biochemical studies show that histamine and phenethylamine moieties were produced from histidine and phenylalanine substrates by a decarboxylase enzyme [41][42][43]. Pseudomobactin A (4) was proposed logically to have formed through direct amination of the unstable salimethyloxazolinyl

Synthetic accesses to biguanide compounds

• Oleksandr Grytsai,
• Cyril Ronco and
• Rachid Benhida

Beilstein J. Org. Chem. 2021, 17, 1001–1040, doi:10.3762/bjoc.17.82

• cyanoguanidines and amine hydrochlorides: One example of the direct fusion of a phenethylamine hydrochloride derivative and a substituted cyanoguanidine has been recently disclosed by Kim et al. (Scheme 15) [27]. After 2 h reaction time, the yield proved excellent. Heating of substituted cyanoguanidines and

From dipivaloylketene to tetraoxaadamantanes

• Gert Kollenz and
• Curt Wentrup

Beilstein J. Org. Chem. 2018, 14, 1–10, doi:10.3762/bjoc.14.1

• exhibit axial chirality [21], as has been demonstrated by 1H NMR spectroscopy using the optically active shift reagent Eu(hfc)3 [19]. The enantiomers of the dicarboxylic acid 11 have been separated by flash chromatography of their diastereomeric salts with 1-phenethylamine, and the structures of the acids

Quinone-catalyzed oxidative deformylation: synthesis of imines from amino alcohols

• Xinyun Liu,
• Johnny H. Phan,
• Benjamin J. Haugeberg,
• Shrikant S. Londhe and
• Michael D. Clift

Beilstein J. Org. Chem. 2017, 13, 2895–2901, doi:10.3762/bjoc.13.282

• . Phenethylamine (6q) provided only a 17% yield of the corresponding imine (7q, Table 3, entry 7), potentially due to its increased nucleophilicity, which may result in inhibition of catalysis via condensation with quinone 2c. We also tested several electron deficient amides (6r−t) in these reactions (Table 3

Brønsted acid-mediated cyclization–dehydrosulfonylation/reduction sequences: An easy access to pyrazinoisoquinolines and pyridopyrazines

• Ramana Sreenivasa Rao and
• Chinnasamy Ramaraj Ramanathan

Beilstein J. Org. Chem. 2017, 13, 428–440, doi:10.3762/bjoc.13.46

• the reported procedure [39]. The N-protected N-phenethylpiperazine-2,6-dione 8h was formed, while treating the potassium salt of N-benzyliminodiacetic acid with phenethylamine in presence of CDI in THF under reflux conditions. Similarly, this strategy has been extended to couple arylethylamines with

Phosphated cyclodextrins as water-soluble chiral NMR solvating agents for cationic compounds

• Cira Mollings Puentes and
• Thomas J. Wenzel

Beilstein J. Org. Chem. 2017, 13, 43–53, doi:10.3762/bjoc.13.6

• structural features are examined and enantiomeric differentiation obtained with P-CDs is compared to prior results acquired with CM-CDs. Results and Discussion Thirty-three substrates including α-methylbenzylamine (1), N,α-dimethylbenzylamine (2), N,N-dimethyl-1-phenethylamine (3), N-allyl-α

Recent developments in copper-catalyzed radical alkylations of electron-rich π-systems

• Kirk W. Shimkin and
• Donald A. Watson

Beilstein J. Org. Chem. 2015, 11, 2278–2288, doi:10.3762/bjoc.11.248

• phenethylamine derivatives, many of which possess known biological activity. For instance, reduction of the fully substituted nitroalkane 19 provides phentermine (20), a clinically prescribed appetite suppressant (Scheme 4) [29][30]. While the precise mechanism of this transformation is not fully understood

trans-2-(2,5-Dimethoxy-4-iodophenyl)cyclopropylamine and trans-2-(2,5-dimethoxy-4-bromophenyl)cyclopropylamine as potent agonists for the 5-HT₂ receptor family

• Adam Pigott,
• Stewart Frescas,
• John D. McCorvy,
• Xi-Ping Huang,
• Bryan L. Roth and
• David E. Nichols

Beilstein J. Org. Chem. 2012, 8, 1705–1709, doi:10.3762/bjoc.8.194

• than for DOI itself. Keywords: cyclopropanation; diazomethane; hallucinogen; 5-HT2A agonist; receptor probe; trans-2-phenylcyclopropylamines; Introduction Among the molecules that have proven very valuable to neuroscientists studying brain serotonin systems is the substituted phenethylamine

Molecular recognition of organic ammonium ions in solution using synthetic receptors

• Andreas Späth and
• Burkhard König

Beilstein J. Org. Chem. 2010, 6, No. 32, doi:10.3762/bjoc.6.32

• binding constant of 7.8 × 103 M−1 was found for the complex of phenyl substituted (R,R)-30 with the R-enantiomer of the guest. Chiral side arms derived from phenethylamine attached to diaza-18-crown-6 ethers 31 (Figure 17) effectively enable the molecular recognition of aromatic amino acid potassium and