Carbonylative synthesis and functionalization of indoles

• Alex De Salvo,
• Raffaella Mancuso and
• Xiao-Feng Wu

Beilstein J. Org. Chem. 2024, 20, 973–1000, doi:10.3762/bjoc.20.87

• recent achievements on the synthesis and functionalization of indole derivatives via carbonylative approaches. Keywords: carbonylation; functionalization; indole; metal catalyst; organometallic chemistry; Introduction Indole is a heterocyclic compound consisting of a benzene ring fused with a pyrrole

Syntheses of novel pyridine-based low-molecular-weight luminogens possessing aggregation-induced emission enhancement (AIEE) properties

• Masayori Hagimori,
• Tatsusada Yoshida,
• Yasuhisa Nishimura,
• Yukiko Ogawa and
• Keitaro Tanaka

Beilstein J. Org. Chem. 2022, 18, 580–587, doi:10.3762/bjoc.18.60

• have been reported [7][8][9][10]. Because the aggregated state of AIEE-based compounds is affected by the external environment, these compounds have found use in clinical applications as chemical sensors or fluorescent probes [7][8][9][10]. Pyridine is a nitrogen-containing heterocyclic compound found

Flow synthesis of oxadiazoles coupled with sequential in-line extraction and chromatography

• Kian Donnelly and
• Marcus Baumann

Beilstein J. Org. Chem. 2022, 18, 232–239, doi:10.3762/bjoc.18.27

• poly-heterocyclic compound 2m in low yield (Scheme 4). Having investigated the substrate scope in continuous flow mode, we then moved to probe the scalability of the reaction. A primary advantage of carrying out a reaction in continuous flow is the ease of which it can subsequently be scaled-up

Cerium-photocatalyzed aerobic oxidation of benzylic alcohols to aldehydes and ketones

• Girish Suresh Yedase,
• Sumit Kumar,
• Jessica Stahl,
• Burkhard König and
• Veera Reddy Yatham

Beilstein J. Org. Chem. 2021, 17, 1727–1732, doi:10.3762/bjoc.17.121

• -dichlorobenzaldehyde (2w) in 70% yield. The sulfur-containing compounds 4-(phenylthio)benzyl alcohol (1r) and the heterocyclic compound thiophene-2-ylmethanol (1x) gave the corresponding aldehydes 2r and 2x in 61 and 80% yield, respectively. Finally, 2-naphthylmethanol (1y) was subjected to the reaction conditions and

Heterogeneous photocatalytic cyanomethylarylation of alkenes with acetonitrile: synthesis of diverse nitrogenous heterocyclic compounds

• Guanglong Pan,
• Qian Yang,
• Wentao Wang,
• Yurong Tang and
• Yunfei Cai

Beilstein J. Org. Chem. 2021, 17, 1171–1180, doi:10.3762/bjoc.17.89

• ) ester as a radical initiator, allows the efficient construction of a broad array of structural diverse nitrogenous heterocyclic compounds including indolines, oxindoles, isoquinolinones, and isoquinolinediones. Keywords: carbon nitride; cyanoalkylarylation; heterocyclic compound; heterogeneous

Synthesis and properties of quinazoline-based versatile exciplex-forming compounds

• Rasa Keruckiene,
• Simona Vekteryte,
• Ervinas Urbonas,
• Matas Guzauskas,
• Eigirdas Skuodis,
• Dmytro Volyniuk and
• Juozas V. Grazulevicius

Beilstein J. Org. Chem. 2020, 16, 1142–1153, doi:10.3762/bjoc.16.101

• is to employ both donor and acceptor moieties in a single molecular structure [1][2][3][4]. Quinazoline is a planar aromatic heterocyclic compound with the fused bicyclic structure consisting of benzene and pyrimidine rings. Quinazoline derivatives were investigated and used in medicinal applications

Preparation of 2-phospholene oxides by the isomerization of 3-phospholene oxides

• Péter Bagi,
• Réka Herbay,
• Nikolett Péczka,
• Zoltán Mucsi,
• István Timári and
• György Keglevich

Beilstein J. Org. Chem. 2020, 16, 818–832, doi:10.3762/bjoc.16.75

• antitumor [27][28][29][30], antifungal [31][32] or GABA receptor antagonist activity [33]. The most common synthesis of a given functionalized P-heterocyclic compound comprises the synthesis of the heterocyclic core, followed by its functionalization [27][29][34][35]. This latter step is of special

Emission solvatochromic, solid-state and aggregation-induced emissive α-pyrones and emission-tuneable 1H-pyridines by Michael addition–cyclocondensation sequences

• Natascha Breuer,
• Irina Gruber,
• Christoph Janiak and
• Thomas J. J. Müller

Beilstein J. Org. Chem. 2019, 15, 2684–2703, doi:10.3762/bjoc.15.262

• exert a significant impact on which heterocyclic compound is formed, we also tried to change the electronic nature of the starting material. Therefore, an electron-donating substituent was introduced in the alkynone 3b and the reaction was performed at 75 °C. To our surprise, we only could isolate α

A heteroditopic macrocycle as organocatalytic nanoreactor for pyrroloacridinone synthesis in water

• Piyali Sarkar,
• Sayan Sarkar and
• Pradyut Ghosh

Beilstein J. Org. Chem. 2019, 15, 1505–1514, doi:10.3762/bjoc.15.152

• apoptotic cells, the investigation of the morphology of nuclei, the direct counting of cultivable bacteria, DNA intercalators, etc. [1][2][3][4]. Pyrrole, another biologically active heterocyclic compound, when fused with acridines affords promising bioactive pyrroloacridinone moieties demonstrating

Synthesis of spirocyclic scaffolds using hypervalent iodine reagents

• Fateh V. Singh,
• Priyanka B. Kole,
• Saeesh R. Mangaonkar and
• Samata E. Shetgaonkar

Beilstein J. Org. Chem. 2018, 14, 1778–1805, doi:10.3762/bjoc.14.152

• ). Furthermore, spirolactam was used as intermediate in the synthesis of tricyclic compound 43 possessing a similar structure like that of the naturally occurring heterocyclic compound FR901483 [82]. Wardrop and co-workers [83] developed a new method for the preparation of 1-azaspiranes 47 by treatment of α- and

Continuous-flow synthesis of highly functionalized imidazo-oxadiazoles facilitated by microfluidic extraction

• Ananda Herath and
• Nicholas D. P. Cosford

Beilstein J. Org. Chem. 2017, 13, 239–246, doi:10.3762/bjoc.13.26

• isolation of intermediates. We have shown that the “telescoping” of multiple synthetic steps into a single continuous process provides an efficient method for the production of heterocyclic compound libraries in sufficient quantities for biological screening in high-throughput assay formats as well as

Stereodynamic tetrahydrobiisoindole “NU-BIPHEP(O)”s: functionalization, rotational barriers and non-covalent interactions

• Golo Storch,
• Sebastian Pallmann,
• Frank Rominger and
• Oliver Trapp

Beilstein J. Org. Chem. 2016, 12, 1453–1458, doi:10.3762/bjoc.12.141

• preparation of “NU-BIPHEPs” [23] and related biaryls [24]. Doherty et al. reported the use of various diynes yielding for instance tetrahydrobiindene 1a and N-tosyl-protected tetrahydrobiisoindole 1b as the only N-heterocyclic compound (Figure 1A). Aiming at facile deprotection and enabling subsequent

Recent applications of ring-rearrangement metathesis in organic synthesis

• Sambasivarao Kotha,
• Milind Meshram,
• Priti Khedkar,
• Shaibal Banerjee and
• Deepak Deodhar

Beilstein J. Org. Chem. 2015, 11, 1833–1864, doi:10.3762/bjoc.11.199

• 235 has been used in RRM. To this end, compound 235 was subjected to a RRM under the influence of catalyst 3 to deliver the spiro heterocyclic compound 236 (41%). Similarly, compound 237 was treated with catalyst 2 under the same reaction conditions to produce the spiro heterocycle 238 (91%) (Scheme

Deproto-metallation of N-arylated pyrroles and indoles using a mixed lithium–zinc base and regioselectivity-computed CH acidity relationship

• Mohamed Yacine Ameur Messaoud,
• Ghenia Bentabed-Ababsa,
• Madani Hedidi,
• Aïcha Derdour,
• Floris Chevallier,
• Yury S. Halauko,
• Oleg A. Ivashkevich,
• Vadim E. Matulis,
• Laurent Picot,
• Valérie Thiéry,
• Thierry Roisnel,
• Vincent Dorcet and
• Florence Mongin

Beilstein J. Org. Chem. 2015, 11, 1475–1485, doi:10.3762/bjoc.11.160

• the formed aryl iodides by recourse to transition metal-catalyzed coupling reactions [37]. When bis-heterocyclic compound 1a was reacted in THF for 2 h at room temperature with the lithium–zinc base, in situ prepared from ZnCl2·TMEDA (0.5 equiv) and LiTMP (1.5 equiv), a selective deprotonation at the

The unexpected influence of aryl substituents in N-aryl-3-oxobutanamides on the behavior of their multicomponent reactions with 5-amino-3-methylisoxazole and salicylaldehyde

• Volodymyr V. Tkachenko,
• Elena A. Muravyova,
• Sergey M. Desenko,
• Oleg V. Shishkin,
• Svetlana V. Shishkina,
• Dmytro O. Sysoiev,
• Thomas J. J. Müller and
• Valentin A. Chebanov

Beilstein J. Org. Chem. 2014, 10, 3019–3030, doi:10.3762/bjoc.10.320

• ultrasonication at room temperature for 4 h gave exclusively N-(2-methoxyphenyl)-1,5-dimethyl-5,11-dihydro-4H-5,11-methanobenzo[g]isoxazolo[5,4-d][1,3]oxazocine-12-carboxamide (6a) in 66% yield (Scheme 3), while the absence of the isomeric heterocyclic compound 5a was proven by means of TLC and NMR spectroscopy

Recent advances in the electrochemical construction of heterocycles

• Robert Francke

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

• anodically generated 1,2-benzoquinone undergoes a Michael reaction with 62 under formation of adduct 63, which is further oxidized to give benzoquinone 64. Finally, anellation proceeds in a second Michael addition step under formation of heterocyclic compound 65. In the reported cases, both the generation of

Synthesis of ethoxy dibenzooxaphosphorin oxides through palladium-catalyzed C(sp²)–H activation/C–O formation

• Seohyun Shin,
• Dongjin Kang,
• Woo Hyung Jeon and
• Phil Ho Lee

Beilstein J. Org. Chem. 2014, 10, 1220–1227, doi:10.3762/bjoc.10.120

• We report an efficient Pd-catalyzed C(sp2)–H activation/C–O bond formation for the synthesis of ethoxy dibenzooxaphosphorin oxides from 2-(aryl)arylphosphonic acid monoethyl esters under aerobic conditions. Keywords: C–H activation; catalysis; cyclization; palladium; phosphorus heterocyclic compound

A combined continuous microflow photochemistry and asymmetric organocatalysis approach for the enantioselective synthesis of tetrahydroquinolines

• Erli Sugiono and
• Magnus Rueping

Beilstein J. Org. Chem. 2013, 9, 2457–2462, doi:10.3762/bjoc.9.284

• synthesis have been developed. Among the synthetic protocols developed for the preparation of optically active tetrahydroquinolines, the asymmetric hydrogenation of substituted quinolines represents the most widely used and efficient method to prepare this class of N-heterocyclic compound [5][6][7][8][9][10