Tosylhydrazine-promoted self-conjugate reduction–Michael/aldol reaction of 3-phenacylideneoxindoles towards dispirocyclopentanebisoxindole derivatives

• Sayan Pramanik and
• Chhanda Mukhopadhyay

Beilstein J. Org. Chem. 2022, 18, 469–478, doi:10.3762/bjoc.18.49

• ][10][11][12][13][14]. Among the known synthetic methodologies, the domino cycloaddition reaction of benzimidazolium salts with two molecules of 2-(2-oxoindolin-3-ylidene)acetates provided as an important tool for the construction of dispirooxindoles [15]. In particular, most of the dispirooxindole

• . Again, in 2018, Yang et al. [26] synthesized functionalized dispiro[indoline-3,1-cyclopentane-3,3-indolines] via cyclodimerization of 3-phenacylideneoxindolines with benzoyl hydrazides and arylhydrazines. Encouraged by these synthetic methodologies and in continuation to our efforts towards the

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

• employing two equivalents of isoxazolylamines in aqueous solution under reflux with HCl catalysis, resulting in bis(isoxazolyl)naphthoquinones 29 (Scheme 6). The development of synthetic methodologies for the preparation of many bioactive substances is still a challenge. The main issues in synthetic organic

Efficient N-arylation of 4-chloroquinazolines en route to novel 4-anilinoquinazolines as potential anticancer agents

• Rodolfo H. V. Nishimura,
• Thiago dos Santos,
• Valter E. Murie,
• Luciana C. Furtado,
• Leticia V. Costa-Lotufo and
• Giuliano C. Clososki

Beilstein J. Org. Chem. 2021, 17, 2968–2975, doi:10.3762/bjoc.17.206

• antitumor agents, several synthetic methodologies have been developed to prepare these compounds. Amination using primary [6][8][9][10][11][12][13] or secondary [14][15][16] amines and 4-chloroquinazolines is among the most employed procedures. Electron-rich amines (e.g., primary aliphatic amines or hydroxy

DABCO-promoted photocatalytic C–H functionalization of aldehydes

• Bruno Maia da Silva Santos,
• Mariana dos Santos Dupim,
• Cauê Paula de Souza,
• Thiago Messias Cardozo and
• Fernanda Gadini Finelli

Beilstein J. Org. Chem. 2021, 17, 2959–2967, doi:10.3762/bjoc.17.205

• interchanging steps, often required in traditional synthetic methodologies [1][2]. The development of photocatalysis enabled inexpensive access to C–H activation methodologies under mild conditions, with hydrogen atom transfer (HAT) reactions standing out as a main strategy [1][3][4]. The hydrogen abstractor is

Exfoliated black phosphorous-mediated CuAAC chemistry for organic and macromolecular synthesis under white LED and near-IR irradiation

• Azra Kocaarslan,
• Zafer Eroglu,
• Önder Metin and
• Yusuf Yagci

Beilstein J. Org. Chem. 2021, 17, 2477–2487, doi:10.3762/bjoc.17.164

• has set a milestone as a new and effective method for the synthesis of macromolecules [11]. Initiation of this reaction photocatalytically provides many advantages for the synthetic methodologies including bioconjugation, labeling, surface functionalization, dendrimer synthesis, polymer synthesis, and

Efficient synthesis of polyfunctionalized carbazoles and pyrrolo[3,4-c]carbazoles via domino Diels–Alder reaction

• Ren-Jie Fang,
• Chen Yan,
• Jing Sun,
• Ying Han and
• Chao-Guo Yan

Beilstein J. Org. Chem. 2021, 17, 2425–2432, doi:10.3762/bjoc.17.159

• hand, carbazole derivatives also have potential applications in optoelectronic materials, conducting polymers, and synthetic dyes [9][10][11]. Over the past decades, many efficient synthetic methodologies for functionalized carbazole derivatives have been successfully developed [12][13][14][15][16][17

Strategies for the synthesis of brevipolides

• Yudhi D. Kurniawan and
• A'liyatur Rosyidah

Beilstein J. Org. Chem. 2021, 17, 2399–2416, doi:10.3762/bjoc.17.157

• human cancer cell lines and inhibition of the chemokine receptor CCR5, make them attractive synthetic targets. This review article highlights the recent synthetic methodologies and briefly summarizes their biological activities. Keywords: brevipolides; 5,6-dihydro-α-pyrone; Furukawa-modified Simmons

• design new synthetic methodologies for reproducing these natural products and their analogues as well as to develop new pharmaceuticals from them. Structures of brevipolides A–O (1 – 15). Retrosynthetic analysis of brevipolide H (8) by Kumaraswamy. Attempt to synthesize brevipolide H (8) by Kumaraswamy

Synthesis and antimicrobial activity of 1H-1,2,3-triazole and carboxylate analogues of metronidazole

• Satya Kumar Avula,
• Syed Raza Shah,
• Khdija Al-Hosni,
• Muhammad U. Anwar,
• Rene Csuk,
• Biswanath Das and
• Ahmed Al-Harrasi

Beilstein J. Org. Chem. 2021, 17, 2377–2384, doi:10.3762/bjoc.17.154

• develop new synthetic methodologies toward the 1H-1,2,3-triazole group containing organic entities. However, earlier methods of the synthesis of aliphatic and aromatic esters of metronidazole are associated with different drawbacks such as long conversion times, low yields and preparation of their

A novel methodology for the efficient synthesis of 3-monohalooxindoles by acidolysis of 3-phosphate-substituted oxindoles with haloid acids

• Li Liu,
• Yue Li,
• Tiao Huang,
• Dulin Kong and
• Mingshu Wu

Beilstein J. Org. Chem. 2021, 17, 2321–2328, doi:10.3762/bjoc.17.150

• industrial application. Representation of bioactive molecules and applications. Synthetic methodologies for 3-monohalooxindoles. Substrate scope of the acidolysis of isatin-derived phosphates 2 with hydrochloric acid. Standard reaction conditions: 2a–r (0.5 mmol), respectively, hydrochloric acid (7.5 mmol

On the application of 3d metals for C–H activation toward bioactive compounds: The key step for the synthesis of silver bullets

• Renato L. Carvalho,
• Amanda S. de Miranda,
• Mateus P. Nunes,
• Roberto S. Gomes,
• Guilherme A. M. Jardim and
• Eufrânio N. da Silva Júnior

Beilstein J. Org. Chem. 2021, 17, 1849–1938, doi:10.3762/bjoc.17.126

• few of them become approved, due to their toxicity or other issues related to their applicability. Therefore, synthetic methodologies that facilitate the successful production of potential biologically active molecules have a relevant role in the organic synthesis research field. One of the key

• synthetic methodologies is the C–H bond activation process that enables a straightforward access to several important and innovative compounds [14][15][16][17][18]. In the last few years, metals such as ruthenium [19][20][21], rhodium [22][23][24], palladium [25][26][27], and iridium [28][29][30] have been

2,4-Bis(arylethynyl)-9-chloro-5,6,7,8-tetrahydroacridines: synthesis and photophysical properties

• Najeh Tka,
• Mohamed Adnene Hadj Ayed,
• Mourad Ben Braiek,
• Mahjoub Jabli,
• Noureddine Chaaben,
• Kamel Alimi,
• Stefan Jopp and
• Peter Langer

Beilstein J. Org. Chem. 2021, 17, 1629–1640, doi:10.3762/bjoc.17.115

• ][38][39] and were reported to be promising candidates for potential use as organic light emitting diodes [40]. Thus, various synthetic methodologies for the preparation of acridine-based molecules have been developed [41][42][43][44][45][46][47]. Tetrahydroacridine, containing a partially hydrogenated

Methodologies for the synthesis of quaternary carbon centers via hydroalkylation of unactivated olefins: twenty years of advances

• Thiago S. Silva and
• Fernando Coelho

Beilstein J. Org. Chem. 2021, 17, 1565–1590, doi:10.3762/bjoc.17.112

• activation. The use of metals in which the protodemetalation step of the σ-alkylmetal complex occurs preferentially to the β-hydride elimination arose as an alternative for the development of new methodologies. During the early 2000s, several synthetic methodologies flourished that employed gold catalysis to

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

• pentofuranosyl sugar moiety. Various synthetic methodologies have been developed for the introduction of the additional nucleobase/heterocyclic system directly or via a linker at the C-2′/C-3′/C-4′/C-5′ position of the pentofuranosyl moieties. We have categorized the double-headed furanosyl-nucleosides depending

• , Bose Institute, P1/12 CIT Scheme VIIM, Kolkata-700 054, India 10.3762/bjoc.17.98 Abstract Double-headed nucleoside monomers have immense applications for studying secondary nucleic acid structures. They are also well-known as antimicrobial agents. This review article accounts for the synthetic

• methodologies and the biological applications of double-headed nucleosides. Keywords: acyclic double-headed nucleosides; bicyclic double-headed nucleosides; furanosyl double-headed nucleosides; modified nucleosides; pyranosyl double-headed nucleosides; Introduction Nucleosides are the constructional subunits

Design, synthesis and photophysical properties of novel star-shaped truxene-based heterocycles utilizing ring-closing metathesis, Clauson–Kaas, Van Leusen and Ullmann-type reactions as key tools

• Shakeel Alvi and
• Rashid Ali

Beilstein J. Org. Chem. 2021, 17, 1374–1384, doi:10.3762/bjoc.17.96

• metathesis, Ullmann-type coupling, Clauson–Kaas, and Van Leusen reactions as crucial transformations. Synthetic Strategy Basically, our endeavor toward the synthesis of truxene-based systems has been rooted in the development of new synthetic methodologies to assemble diverse polycyclic as well as

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

• . Asymmetric synthesis of pyrrolidines The pyrrolidine ring is more represented within natural products than the 3- and 4-membered nitrogen-containing heterocycles. This molecular array is also found in drugs and other biologically active molecules. For this reason, there are numerous examples of synthetic

• methodologies for these compounds in the literature. In most cases, the pyrrolidine ring is formed from an amine with a hydrocarbon chain that also carries a functional group at the appropriate distance that allows the cyclization process to take place. In the case of substituted pyrrolidines, the

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

• critical overview of the synthetic accesses to biguanide compounds, as well as their comparative advantages and limitations. It also underlines the need of developing new synthetic methodologies to reach a wider variety of biguanides and to overcome the underrepresentation of these compounds. Keywords

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

• inhibitors of α-glycosidases [11][19]. Recent reviews report on the latest synthetic methodologies for aminocyclitols and related compounds [1][2][3][16]. Many methods have been previously reported for the synthesis of aminocyclitols containing five- and six-membered rings, along with their diverse

A new and efficient methodology for olefin epoxidation catalyzed by supported cobalt nanoparticles

• Lucía Rossi-Fernández,
• Viviana Dorn and
• Gabriel Radivoy

Beilstein J. Org. Chem. 2021, 17, 519–526, doi:10.3762/bjoc.17.46

• heterogeneous catalysts [27] that are wide in substrate scope, active enough and highly selective. As part of our continuing interest in the development of new synthetic methodologies based on the use of catalysis by non-noble transition metal nanoparticles (MNPs) for their application in a wide range of

1,2,3-Triazoles as leaving groups: S_NAr reactions of 2,6-bistriazolylpurines with O- and C-nucleophiles

• Dace Cīrule,
• Irina Novosjolova,
• Ērika Bizdēna and
• Māris Turks

Beilstein J. Org. Chem. 2021, 17, 410–419, doi:10.3762/bjoc.17.37

• ][3][4][5][6]. They are often used as antiviral, anticancer and antibacterial agents. Such intensive medicinal chemistry applications demand for constant development of novel synthetic methodologies. Frequently, the purine structure is modified in SNAr reactions with N- [7][8][9][10][11] and S

A sustainable strategy for the straightforward preparation of 2H-azirines and highly functionalized NH-aziridines from vinyl azides using a single solvent flow-batch approach

• Michael Andresini,
• Leonardo Degannaro and
• Renzo Luisi

Beilstein J. Org. Chem. 2021, 17, 203–209, doi:10.3762/bjoc.17.20

• risks [6]. Recently, a variety of sustainable solvents has been therefore identified, and their use have been combined with those of enabling technologies. In this scenario, the development of continuous flow synthetic methodologies has found its fortune in the past two decades [7][8][9]. Several

Progress in the total synthesis of inthomycins

• Bidyut Kumar Senapati

Beilstein J. Org. Chem. 2021, 17, 58–82, doi:10.3762/bjoc.17.7

• present review provides a systematic summary of synthetic strategies for the synthesis of inthomycins and their analogues over the period of 1999 to present. Rewiew Synthesis Undoubtedly, the unique skeleton of inthomycins has acted as an inspiration for the development of new synthetic methodologies

Recent progress in the synthesis of homotropane alkaloids adaline, euphococcinine and N-methyleuphococcinine

• Dimas J. P. Lima,
• Antonio E. G. Santana,
• Michael A. Birkett and
• Ricardo S. Porto

Beilstein J. Org. Chem. 2021, 17, 28–41, doi:10.3762/bjoc.17.4

• provide enantiomerically pure alkaloids. Therefore, homotropane-based compounds continue to attract the attention of researchers involved in the progress for new synthetic methodologies to reproduce these natural products and synthesize their analogs, improving existing methods. Homotropane

An atom-economical addition of methyl azaarenes with aromatic aldehydes via benzylic C(sp³)–H bond functionalization under solvent- and catalyst-free conditions

• Divya Rohini Yennamaneni,
• Vasu Amrutham,
• Krishna Sai Gajula,
• Rammurthy Banothu,
• Murali Boosa and
• Narender Nama

Beilstein J. Org. Chem. 2020, 16, 3093–3103, doi:10.3762/bjoc.16.259

• reevaluated. Therefore, alternatives with environmentally benign reagents are much in focus. Correspondingly, considering the exemplar shift from conventional synthetic methodologies towards green chemistry, there have been some alternatives or replacements of toxic catalysts and hazardous solvents in

Synthesis of imidazo[1,5-a]pyridines via cyclocondensation of 2-(aminomethyl)pyridines with electrophilically activated nitroalkanes

• Dmitrii A. Aksenov,
• Nikolai A. Arutiunov,
• Vladimir V. Maliuga,
• Alexander V. Aksenov and
• Michael Rubin

Beilstein J. Org. Chem. 2020, 16, 2903–2910, doi:10.3762/bjoc.16.239

• Within the last few years, we have developed and implemented a number of novel synthetic methodologies in our laboratories, involving acid-mediated cascade transformations of nitroalkenes and nitroalkanes, which target materials science and medicinal chemistry applications. It was demonstrated that upon

Synthesis of novel fluorinated building blocks via halofluorination and related reactions

• Attila Márió Remete,
• Tamás T. Novák,
• Melinda Nonn,
• Matti Haukka,
• Ferenc Fülöp and
• Loránd Kiss

Beilstein J. Org. Chem. 2020, 16, 2562–2575, doi:10.3762/bjoc.16.208

• cyclic olefins, such as diesters, imides, and lactams with varied functionalization patterns and different structural architectures is described. The synthetic methodologies were based on electrophilic activation through halonium ions of the ring olefin bonds, followed by nucleophilic fluorination with