Construction of diazepine-containing spiroindolines via annulation reaction of α-halogenated N-acylhydrazones and isatin-derived MBH carbonates

• Xing Liu,
• Wenjing Shi,
• Jing Sun and
• Chao-Guo Yan

Beilstein J. Org. Chem. 2023, 19, 1923–1932, doi:10.3762/bjoc.19.143

• readily available reagents, mild conditions, satisfactory yields, broad substrate scope, high molecular convergence, and atomic economy. The synthetic applications of this annulation reaction in heterocyclic chemistry might be significant. Experimental General procedure for the preparation of dihydrospiro

Unprecedented synthesis of a 14-membered hexaazamacrocycle

• Anastasia A. Fesenko and
• Anatoly D. Shutalev

Beilstein J. Org. Chem. 2023, 19, 1728–1740, doi:10.3762/bjoc.19.126

• structure and reactivity of the obtained macrocycle are outlined. Keywords: amidrazones; hexaazamacrocycles; pyrazolo[3,4-d]pyrimidines; ring contraction; self-assembly; Introduction The chemistry of polyazamacrocycles (PAMs) is currently one of the most rapidly developing areas of heterocyclic chemistry

Selective construction of dispiro[indoline-3,2'-quinoline-3',3''-indoline] and dispiro[indoline-3,2'-pyrrole-3',3''-indoline] via three-component reaction

• Ziying Xiao,
• Fengshun Xu,
• Jing Sun and
• Chao-Guo Yan

Beilstein J. Org. Chem. 2023, 19, 1234–1242, doi:10.3762/bjoc.19.91

• . This reaction has the advantages of using readily available materials, simple reaction conditions, satisfactory yields, high diastereoselectivity and atomic economy, which enable this reaction potential synthetic applications in heterocyclic chemistry and medicinal chemistry. Experimental General

Catalytic aza-Nazarov cyclization reactions to access α-methylene-γ-lactam heterocycles

• Bilge Banu Yagci,
• Selin Ezgi Donmez,
• Onur Şahin and
• Yunus Emre Türkmen

Beilstein J. Org. Chem. 2023, 19, 66–77, doi:10.3762/bjoc.19.6

• -heterocycles [39][40][41][42][43][44][45] and specifically α-methylene-γ-lactams as a subset of this compound class, are popular targets in heterocyclic chemistry and drug discovery [46][47][48][49][50][51][52][53][54][55][56]. Against this background, we herein disclose a full account of our studies on the

Microwave-assisted multicomponent reactions in heterocyclic chemistry and mechanistic aspects

• Shivani Gulati,
• Stephy Elza John and
• Nagula Shankaraiah

Beilstein J. Org. Chem. 2021, 17, 819–865, doi:10.3762/bjoc.17.71

Microwave-assisted efficient one-pot synthesis of N²-(tetrazol-5-yl)-6-aryl/heteroaryl-5,6-dihydro-1,3,5-triazine-2,4-diamines

• Moustafa Sherief Moustafa,
• Ramadan Ahmed Mekheimer,
• Saleh Mohammed Al-Mousawi,
• Mohamed Abd-Elmonem,
• Hesham El-Zorba,
• Afaf Mohamed Abdel Hameed,
• Tahany Mahmoud Mohamed and
• Kamal Usef Sadek

Beilstein J. Org. Chem. 2020, 16, 1706–1712, doi:10.3762/bjoc.16.142

• green methodologies in synthetic heterocyclic chemistry. The utilization of microwave heating as an energy source has several advantages including operational simplicity, high reaction yields, enhanced rates, and increased energy efficiency [34][35][36][37][38][39][40]. In continuation of our efforts in

Multicomponent reactions III

• Thomas J. J. Müller

Beilstein J. Org. Chem. 2019, 15, 1974–1975, doi:10.3762/bjoc.15.192

• of synthetic efficiency. Biologically and pharmaceutically relevant scaffolds are likewise tackled as chromophores, methodology development and conceptual design of macro(hetero)cycles go hand in hand with MCR-based heterocyclic chemistry. As in the previous thematic issues also this issue opens the

The LANCA three-component reaction to highly substituted β-ketoenamides – versatile intermediates for the synthesis of functionalized pyridine, pyrimidine, oxazole and quinoxaline derivatives

• Tilman Lechel,
• Roopender Kumar,
• Mrinal K. Bera,
• Reinhold Zimmer and
• Hans-Ulrich Reissig

Beilstein J. Org. Chem. 2019, 15, 655–678, doi:10.3762/bjoc.15.61

• of different heterocycles that were generated from the two β-ketoenamides KE20 and KE61 and shows the potential of these methods in heterocyclic chemistry. Options for palladium-catalyzed reactions are also offered by compound PM60 that was prepared from mono-pyrimidyl-substituted β-ketoenamide PM38

A convenient and practical synthesis of β-diketones bearing linear perfluorinated alkyl groups and a 2-thienyl moiety

• Ilya V. Taydakov,
• Yuliya M. Kreshchenova and
• Ekaterina P. Dolotova

Beilstein J. Org. Chem. 2018, 14, 3106–3111, doi:10.3762/bjoc.14.290

• extractants in solvent–solvent extraction processes [4], in preparation of volatile complexes for chemical vapour deposition (CVD) technique [5][6], in syntheses of luminescent compounds [7], as starting materials in organic and heterocyclic chemistry [8][9] and in many other practical applications [10][11

The reductive decyanation reaction: an overview and recent developments

• Jean-Marc R. Mattalia

Beilstein J. Org. Chem. 2017, 13, 267–284, doi:10.3762/bjoc.13.30

• ether cleavage. Aluminium- and borohydrides and the use of sodium hydride Reduction of α-aminonitriles Bifunctional α-aminonitriles exhibit several modes of reactivity. Recent reviews demonstrated the richness of this chemistry and emphasized synthetic applications particularly in heterocyclic chemistry

• range of nitriles including the most challenging alkanenitriles and allow a large functional group tolerance. The decyanation of α-aminonitriles by aluminium- and borohydrides has been widely investigated and offers synthetic applications in heterocyclic chemistry. Recent developments using N

Multicomponent reactions: A simple and efficient route to heterocyclic phosphonates

• Mohammad Haji

Beilstein J. Org. Chem. 2016, 12, 1269–1301, doi:10.3762/bjoc.12.121

• azide–alkyne cycloadditions and various A3-coupling reactions are useful procedures in heterocyclic chemistry. However, several methods based on these protocols have also been developed for the synthesis of heterocyclic phosphonates. The 1,2-dihydroisoquinolin-1-ylphosphonates 172 were formed through a

Life lessons

• Jonathan R. Nitschke

Beilstein J. Org. Chem. 2015, 11, 2350–2354, doi:10.3762/bjoc.11.256

• with a tutorial-style course on heterocyclic chemistry by J. Hodge Markgraf. Two summers stand out in my memory, when I carried out internships at Nanoptics, a company in Gainesville that makes optical fiber and various devices that incorporate it. The company was small enough at the time for me to

3-Glucosylated 5-amino-1,2,4-oxadiazoles: synthesis and evaluation as glycogen phosphorylase inhibitors

• Marion Donnier-Maréchal,
• David Goyard,
• Vincent Folliard,
• Tibor Docsa,
• Pal Gergely,
• Jean-Pierre Praly and
• Sébastien Vidal

Beilstein J. Org. Chem. 2015, 11, 499–503, doi:10.3762/bjoc.11.56

• very recently reported in the context of heterocyclic chemistry [29] and we have applied it with success to our GP inhibitor design. The dimethylamino group (Scheme 1, a) was chosen as a small pharmacophore that can be readily accommodated in the GP’s catalytic site. Aromatic moieties were also

Bis(vinylenedithio)tetrathiafulvalene analogues of BEDT-TTF

• Erdal Ertas,
• İlknur Demirtas and
• Turan Ozturk

Beilstein J. Org. Chem. 2015, 11, 403–415, doi:10.3762/bjoc.11.46

• target materials, having interesting electronic properties, but also illustrated challenging synthetic heterocyclic chemistry. Chemical structure of the TTF analogues and TCNQ. Oxidation states of TTF. 1,4-Dithiin and thiophene fused TTF analogues from 1,8-diketone. Reaction mechanism of fused 1,4

A simple and efficient method for the preparation of 5-hydroxy-3-acyltetramic acids

• Johanna Trenner and
• Evgeny V. Prusov

Beilstein J. Org. Chem. 2015, 11, 323–327, doi:10.3762/bjoc.11.37

• oxygen is reported. The deprotection of the resulting compounds was also achieved. Keywords: heterocyclic chemistry; hydroxylation; natural products; tetramic acids; Findings 5-Hydroxy-3-acyltetramic acid is an unusual structural element which is found in the molecules of such biologically active

Recent advances in the electrochemical construction of heterocycles

• Robert Francke

Beilstein J. Org. Chem. 2014, 10, 2858–2873, doi:10.3762/bjoc.10.303

• heterocyclic compounds is steadily growing, heterocyclic chemistry remains in the focus of the synthetic community. Enormous efforts have been made in the last decades in order to render the production of such compounds more selective and efficient. However, most of the conventional methods for the

• electrochemistry of heterocyclic compounds are also available [27][28][29]. However, recent innovations in electrosynthesis such as the cation pool method or the development of novel electron transfer mediators also have a significant impact on heterocyclic chemistry [30][31]. This review focuses upon both anodic

A simple, enaminone-based approach to some bicyclic pyridazinium tetrafluoroborates

• František Josefík,
• Markéta Svobodová,
• Valerio Bertolasi and
• Petr Šimůnek

Beilstein J. Org. Chem. 2013, 9, 1463–1471, doi:10.3762/bjoc.9.166

• in heterocyclic chemistry (for many reviews see, e.g., [2][3][4][5][6]). During the past several years we have dealt with the reaction of various enaminones with diazonium salts and established a number of methods for the construction of some important or unusual heterocyclic systems [7][8][9][10][11

N-Heterocyclic carbene/Brønsted acid cooperative catalysis as a powerful tool in organic synthesis

• Rob De Vreese and
• Matthias D’hooghe

Beilstein J. Org. Chem. 2012, 8, 398–402, doi:10.3762/bjoc.8.43

• functionalized pyrrolidin-2-ones as valuable scaffolds in heterocyclic chemistry. This Commentary will briefly highlight the concept of N-heterocyclic carbene/Brønsted acid cooperative catalysis as a new and powerful methodology in organic chemistry. Keywords: Brønsted acids; cooperative catalysis; γ-lactams; N

Synthetic approaches to multifunctional indenes

• Neus Mesquida,
• Sara López-Pérez,
• Immaculada Dinarès and
• Ermitas Alcalde

Beilstein J. Org. Chem. 2011, 7, 1739–1744, doi:10.3762/bjoc.7.204

• approaches leading to these compounds lag behind those for heteroaromatic systems, e.g., indoles, being limited as it is by the scarce knowledge of indene chemistry in comparison with heterocyclic chemistry [3][17][18][19][20][21][22]. Moreover, chemical transformation by indenes, which could permit rapid

Multicomponent reactions

• Thomas J. J. Müller

Beilstein J. Org. Chem. 2011, 7, 960–961, doi:10.3762/bjoc.7.107

• elementary organic reactions under similar conditions. Most interestingly, multicomponent reactions have accompanied the field of organic chemistry since the early days, particularly in heterocyclic chemistry, but have not been recognized as a fundamental principle until Ugi's groundbreaking extension of the

Preparation of pyridine-3,4-diols, their crystal packing and their use as precursors for palladium-catalyzed cross-coupling reactions

• Tilman Lechel,
• Irene Brüdgam and
• Hans-Ulrich Reissig

Beilstein J. Org. Chem. 2010, 6, No. 42, doi:10.3762/bjoc.6.42

• applications as potent chelating agents in medicinal chemistry [6]. Furthermore, perfluorinated heteroaromatic compounds are interesting synthetic intermediates for the development of novel pharmaceuticals [7]. Continuing our research on heterocyclic chemistry based on alkoxyallenes [8][9][10][11][12][13][14

The tert- amino effect in heterocyclic chemistry: Synthesis of new fused pyrazolinoquinolizine and 1,4-oxazinopyrazoline derivatives

• Dipak Prajapati and
• Kalyan Jyoti Borah

Beilstein J. Org. Chem. 2007, 3, No. 43, doi:10.1186/1860-5397-3-43

Microwave- assisted ring closure reactions: Synthesis of 8-substituted xanthine derivatives and related pyrimido- and diazepinopurinediones

• Joachim C. Burbiel,
• Jörg Hockemeyer and
• Christa E. Müller

Beilstein J. Org. Chem. 2006, 2, No. 20, doi:10.1186/1860-5397-2-20

• poor mixing. Microwave-assisted synthesis has been extensively applied in the field of heterocyclic chemistry, especially when high temperatures are needed for ring formation with conventional heating [24]. Based on these findings the preparation of 8-substituted xanthine derivatives and related