Systematic synthetic study of four diastereomerically distinct limonene-1,2-diols and their corresponding cyclic carbonates

• Hiroshi Morikawa,
• Jun-ichi Yamaguchi,
• Shun-ichi Sugimura,
• Masato Minamoto,
• Yuuta Gorou,
• Hisatoyo Morinaga and
• Suguru Motokucho

Beilstein J. Org. Chem. 2019, 15, 130–136, doi:10.3762/bjoc.15.13

• significance, largely because LM derivatives with their versatile functionality can be effectively utilised in organic and polymer chemistry. (4R)-Limonene-1,2-diols (LMdiols) are some of the most important LM derivatives because they act as precursors of bioactive molecules [12][13][14]. Furthermore, LMdiol

Cross metathesis-mediated synthesis of hydroxamic acid derivatives

• Shital Kumar Chattopadhyay,
• Subhankar Ghosh and
• Suman Sil

Beilstein J. Org. Chem. 2018, 14, 3070–3075, doi:10.3762/bjoc.14.285

• ), 29.3 (CH2), 29.1 (CH2), 28.9 (CH2), 25.5 (CH2), 22.5 (CH2), 14.3 (C11); HRMS (TOF MS ES+) m/z: [M + Na]+ calcd for C11H23NNaO2, 224.1626; found, 224.1638. Some bioactive molecules containing hydroxamate functionality. Cross metathesis between a class-I alkene and N-benzyloxyacryl amide. Hydroxamates

One-pot synthesis of epoxides from benzyl alcohols and aldehydes

• Edwin Alfonzo,
• Jesse W. L. Mendoza and
• Aaron B. Beeler

Beilstein J. Org. Chem. 2018, 14, 2308–2312, doi:10.3762/bjoc.14.205

• , esters, and ketones (Figure 1). The latter is most likely due to competing enolization of the ketone leading to undesired reactivity [29]. Many of the epoxides that are of interest to us are highly oxygenated on the aryl rings and can be used for the synthesis of numerous bioactive molecules [27][30][31

Revisiting ring-degenerate rearrangements of 1-substituted-4-imino-1,2,3-triazoles

• James T. Fletcher,
• Matthew D. Hanson,
• Joseph A. Christensen and
• Eric M. Villa

Beilstein J. Org. Chem. 2018, 14, 2098–2105, doi:10.3762/bjoc.14.184

• and bioactive molecules, but depending on the substituent identity, it can be inherently unstable due to Dimroth rearrangements. This study examined parameters governing the ring-degenerate rearrangement reactions of 1-substituted-4-imino-1,2,3-triazoles, expanding on trends first observed by L’abbé

Applications of organocatalysed visible-light photoredox reactions for medicinal chemistry

• Michael K. Bogdos,
• Emmanuel Pinard and
• John A. Murphy

Beilstein J. Org. Chem. 2018, 14, 2035–2064, doi:10.3762/bjoc.14.179

• medicinal chemistry. This is a reflection of the tendency of synthetic bioactive molecules to exhibit peptidomimetic properties. Though there is a vast number of procedures that generate amide bonds, an interesting approach is taken by Leow, who has demonstrated the synthesis of amides through the oxidative

Two new 2-alkylquinolones, inhibitory to the fish skin ulcer pathogen Tenacibaculum maritimum, produced by a rhizobacterium of the genus Burkholderia sp.

• Dandan Li,
• Naoya Oku,
• Atsumi Hasada,
• Masafumi Shimizu and
• Yasuhiro Igarashi

Beilstein J. Org. Chem. 2018, 14, 1446–1451, doi:10.3762/bjoc.14.122

• -1 Yanagido, Gifu 501-1193, Japan 10.3762/bjoc.14.122 Abstract Exploration of rhizobacteria of the genus Burkholderia as an under-tapped resource of bioactive molecules resulted in the isolation of two new antimicrobial 2-alkyl-4-quinolones. (E)-2-(Hept-2-en-1-yl)quinolin-4(1H)-one (1) and (E)-2

A selective removal of the secondary hydroxy group from ortho-dithioacetal-substituted diarylmethanols

• Anna Czarnecka,
• Emilia Kowalska,
• Agnieszka Bodzioch,
• Joanna Skalik,
• Marek Koprowski,
• Krzysztof Owsianik and
• Piotr Bałczewski

Beilstein J. Org. Chem. 2018, 14, 1229–1237, doi:10.3762/bjoc.14.105

• cyclic compounds possessing a diarylmethyl motif, like podophyllotoxin (V) and lasofoxifene (VI), have been a subject of interest as bioactive molecules (Figure 1) [1]. The diarylmethane derivatives, isolated from natural sources, showed antibacterial [2], antiestrogenic and antitumorigenic (I) [3][4][5

One hundred years of benzotropone chemistry

• Arif Dastan,
• Haydar Kilic and
• Nurullah Saracoglu

Beilstein J. Org. Chem. 2018, 14, 1120–1180, doi:10.3762/bjoc.14.98

Photocatalytic formation of carbon–sulfur bonds

• Alexander Wimmer and
• Burkhard König

Beilstein J. Org. Chem. 2018, 14, 54–83, doi:10.3762/bjoc.14.4

Reagent-controlled regiodivergent intermolecular cyclization of 2-aminobenzothiazoles with β-ketoesters and β-ketoamides

• Irwan Iskandar Roslan,
• Kian-Hong Ng,
• Gaik-Khuan Chuah and
• Stephan Jaenicke

Beilstein J. Org. Chem. 2017, 13, 2739–2750, doi:10.3762/bjoc.13.270

• wastes. Here we describe the extension of this α-bromination shuttle system to 2-aminobenzothiazoles as substrates to synthesize benzo[d]imidazo[2,1-b]thiazoles. The benzo[d]imidazo[2,1-b]thiazole backbone is found in many bioactive molecules and pharmaceutical compounds as evident by its use as

¹⁵N-Labelling and structure determination of adamantylated azolo-azines in solution

• Sergey L. Deev,
• Alexander S. Paramonov,
• Tatyana S. Shestakova,
• Igor A. Khalymbadzha,
• Oleg N. Chupakhin,
• Julia O. Subbotina,
• Oleg S. Eltsov,
• Pavel A. Slepukhin,
• Vladimir L. Rusinov,
• Alexander S. Arseniev and
• Zakhar O. Shenkarev

Beilstein J. Org. Chem. 2017, 13, 2535–2548, doi:10.3762/bjoc.13.250

• -ones in acidic conditions occurs through the formation of the adamantyl cation. Keywords: adamantylation; azolo-1,2,4-triazines; J-coupling; 15N-labelled; NMR spectra; 1,2,4-triazolo[1,5-a]pyrimidines; Introduction The incorporation of an adamantyl moiety in bioactive molecules and analogues of

Exploring mechanochemistry to turn organic bio-relevant molecules into metal-organic frameworks: a short review

• Vânia André,
• Sílvia Quaresma,
• João Luís Ferreira da Silva and
• M. Teresa Duarte

Beilstein J. Org. Chem. 2017, 13, 2416–2427, doi:10.3762/bjoc.13.239

• bioactive molecules is achieved by degradation of the framework, ii) no multistep synthesis is required as the molecules are part of the matrix itself, iii) synergetic effects between the active molecule and the metal may be explored, and iv) co-delivery of drugs is possible if a porous network is built

• enhancement of MOF structural and stability properties [90][91]. Bioactive molecules like caffeine [92][93] and anticancer drugs [94][95][96][97][98] were incorporated in ZIF-8 and tests proved that these systems allowed for a controlled drug release. Further studies involving ZIF-8 with encapsulated

Solvent-free copper-catalyzed click chemistry for the synthesis of N-heterocyclic hybrids based on quinoline and 1,2,3-triazole

• Martina Tireli,
• Silvija Maračić,
• Stipe Lukin,
• Marina Juribašić Kulcsár,
• Dijana Žilić,
• Mario Cetina,
• Ivan Halasz,
• Silvana Raić-Malić and
• Krunoslav Užarević

Beilstein J. Org. Chem. 2017, 13, 2352–2363, doi:10.3762/bjoc.13.232

• bond bioisosteres made the click reaction a valuable synthetic methodology for conjugation of bioactive molecules [7][8][9] aiming to improve their biological activities [4][10][11]. Discovery of copper(I) ion catalysis in azide–alkyne cycloadditions was decisive for applications of this reaction, as

A mechanochemical approach to access the proline–proline diketopiperazine framework

• Nicolas Pétry,
• Hafid Benakki,
• Eric Clot,
• Pascal Retailleau,
• Farhate Guenoun,
• Fatima Asserar,
• Chakib Sekkat,
• Thomas-Xavier Métro,
• Jean Martinez and
• Frédéric Lamaty

Beilstein J. Org. Chem. 2017, 13, 2169–2178, doi:10.3762/bjoc.13.217

• chemists have used DKPs extensively as a synthetic platform, easily synthesized and stereochemically controlled, for the preparation of small bioactive molecules [4][5]. DKPs have also been considered as chiral auxiliaries in asymmetric synthesis [6]. Furthermore, the rigidity of the DKPs is a unique

High-speed vibration-milling-promoted synthesis of symmetrical frameworks containing two or three pyrrole units

• Marco Leonardi,
• Mercedes Villacampa and
• J. Carlos Menéndez

Beilstein J. Org. Chem. 2017, 13, 1957–1962, doi:10.3762/bjoc.13.190

• relevance of nitrogen heterocycles in the generation of bioactive molecules, medicinal chemists would greatly benefit from the ability to build two heterocyclic systems at both ends of the spacer chain in a single maneuver. Further advantages in terms of synthetic efficiency would be gained if the key

• ” approach to the design of bioactive molecules [18][19][20]. Regarding the pyrrole rings, they were generally methyl-substituted at C-2, but the attachment of functional groups to the methyl substituent was also possible, as shown by the preparation of compounds 1g and 1n. Ketone (compounds 1f and 1j–l) and

Oxidative dehydrogenation of C–C and C–N bonds: A convenient approach to access diverse (dihydro)heteroaromatic compounds

• Santanu Hati,
• Ulrike Holzgrabe and
• Subhabrata Sen

Beilstein J. Org. Chem. 2017, 13, 1670–1692, doi:10.3762/bjoc.13.162

• the synthesis of AZD8926. Catalytic oxidative dehydrogenation of tetrahydroquinolines to afford bioactive molecules. Iodobenzene diacetate-mediated synthesis of β-carboline natural products.

Biomimetic molecular design tools that learn, evolve, and adapt

• David A Winkler

Beilstein J. Org. Chem. 2017, 13, 1288–1302, doi:10.3762/bjoc.13.125

• discovery of new bioactive molecules and materials, with examples. Review Open questions in artificial intelligence (AI) Before describing these AI methods and how they can be used in chemistry, biology and elsewhere, it is instructive to consider some of the “big picture” questions of the AI field. Among

• processes of natural selection, and they are efficient ways of exploring extremely large materials spaces. Although accelerated synthesis and testing methods for bioactive molecules (drugs and agrochemicals) and materials are invaluable for accelerating drug and materials research, they cannot alone solve

The effect of cyclodextrin complexation on the solubility and photostability of nerolidol as pure compound and as main constituent of cabreuva essential oil

• Joyce Azzi,
• Pierre-Edouard Danjou,
• David Landy,
• Steven Ruellan,
• Lizette Auezova,
• Hélène Greige-Gerges and
• Sophie Fourmentin

Beilstein J. Org. Chem. 2017, 13, 835–844, doi:10.3762/bjoc.13.84

• Joyce Azzi Pierre-Edouard Danjou David Landy Steven Ruellan Lizette Auezova Helene Greige-Gerges Sophie Fourmentin Bioactive Molecules Research Group, Doctoral School of Sciences and Technologies, Faculty of Sciences, Jdaidet El-Matn, Lebanese University, Lebanon Unité de Chimie Environnementale

Isoxazole derivatives as new nitric oxide elicitors in plants

• Anca Oancea,
• Emilian Georgescu,
• Florentina Georgescu,
• Alina Nicolescu,
• Elena Iulia Oprita,
• Catalina Tudora,
• Lucian Vladulescu,
• Marius-Constantin Vladulescu,
• Florin Oancea and
• Calin Deleanu

Beilstein J. Org. Chem. 2017, 13, 659–664, doi:10.3762/bjoc.13.65

• ]. The thiophene is a core system of a large number of bioactive molecules such as antineoplastic agents [49], non-steroidal anti-inflammatory drugs [50] or compounds with antibacterial activities against several Gram-positive strains [51]. Thus, 3,5-disubstituted isoxazole derivatives were obtained by

Synthesis of 1-indanones with a broad range of biological activity

• Marika Turek,
• Dorota Szczęsna,
• Marek Koprowski and
• Piotr Bałczewski

Beilstein J. Org. Chem. 2017, 13, 451–494, doi:10.3762/bjoc.13.48

Regiochemistry of cyclocondensation reactions in the synthesis of polyazaheterocycles

• Patrick T. Campos,
• Leticia V. Rodrigues,
• Andrei L. Belladona,
• Caroline R. Bender,
• Juliana S. Bitencurt,
• Fernanda A. Rosa,
• Davi F. Back,
• Helio G. Bonacorso,
• Nilo Zanatta,
• Clarissa P. Frizzo and
• Marcos A. P. Martins

Beilstein J. Org. Chem. 2017, 13, 257–266, doi:10.3762/bjoc.13.29

• ; quinoxalinone; thiazolo[3,2-a]pyrimidinone; Introduction Various syntheses of polyazaheterocycles are described in the literature because they are important components for the preparation of bioactive molecules [1][2][3]. One of the most important synthetic methods towards compounds containing nitrogen atoms

cis-Diastereoselective synthesis of chroman-fused tetralins as B-ring-modified analogues of brazilin

• Dimpee Gogoi,
• Runjun Devi,
• Pallab Pahari,
• Bipul Sarma and
• Sajal Kumar Das

Beilstein J. Org. Chem. 2016, 12, 2816–2822, doi:10.3762/bjoc.12.280

• [2,1-c]chromen-6a-ols 5 (Figure 1) as B-ring-modified analogues of brazilin through the fusion of chroman and tetralin motifs to generate new bioactive molecules. To the best of our knowledge, the stereoselective synthesis of such chroman-fused tetralins has never been reported. Based on the continuous

Stereo- and regioselectivity of the hetero-Diels–Alder reaction of nitroso derivatives with conjugated dienes

• Lucie Brulíková,
• Aidan Harrison,
• Marvin J. Miller and
• Jan Hlaváč

Beilstein J. Org. Chem. 2016, 12, 1949–1980, doi:10.3762/bjoc.12.184

• organic synthesis [15][16][17][18][19][20][21][22][23][24], applications of nitroso hetero-Diels–Alder reactions for the synthesis of azasugars [10], and the utilization of nitroso hetero-Diels–Alder reactions in natural product synthesis [9][25] and the synthesis of bioactive molecules [26]. However

One-pot synthesis of enantiomerically pure N-protected allylic amines from N-protected α-amino esters

• Gastón Silveira-Dorta,
• Sergio J. Álvarez-Méndez,
• Víctor S. Martín and
• José M. Padrón

Beilstein J. Org. Chem. 2016, 12, 957–962, doi:10.3762/bjoc.12.94

• unstable to manipulate. As part of our interest in the synthesis of nitrogen-containing bioactive molecules [15], we developed a simplified version of the Reetz protocol [11] for the synthesis of enantiomerically pure anti-β-amino alcohols [16]. The process circumvents the problem of the instability of the

Determination of formation constants and structural characterization of cyclodextrin inclusion complexes with two phenolic isomers: carvacrol and thymol

• Miriana Kfoury,
• David Landy,
• Steven Ruellan,
• Lizette Auezova,
• Hélène Greige-Gerges and
• Sophie Fourmentin

Beilstein J. Org. Chem. 2016, 12, 29–42, doi:10.3762/bjoc.12.5

• Miriana Kfoury David Landy Steven Ruellan Lizette Auezova Helene Greige-Gerges Sophie Fourmentin Bioactive Molecules Research Group, Doctoral School of Science and Technology, Department of Chemistry and Biochemistry, Faculty of Sciences, section II, Lebanese University, Lebanon Unité de Chimie