Decarboxylative 1,3-dipolar cycloaddition of amino acids for the synthesis of heterocyclic compounds

• Xiaofeng Zhang,
• Xiaoming Ma and
• Wei Zhang

Beilstein J. Org. Chem. 2023, 19, 1677–1693, doi:10.3762/bjoc.19.123

• -type AMYs in multicomponent, one-pot, and stepwise reactions for the synthesis of diverse heterocycles related to some bioactive compounds and natural products. Keywords: [3 + 2] cycloaddition; decarboxylation; 1,3-dipolar; double cycloaddition; one-pot synthesis; multicomponent reaction; semi

• aldehydes and alkenes. The first cycloaddition products 3c or 3d can also be used as intermediates for other transformations to synthesize novel heterocyclic rings via multicomponent, one-pot, and stepwise synthesis [63][64]. Presented in the following sections is our work on the development of amino acid

• -based decarboxylative [3 + 2] cycloadditions of N–H-type AMYs B3 and B4 for double cycloadditions. The stereochemistry of the cycloadditions and the combination of the cycloaddition with other transformations to be one-pot or stepwise reactions are also presented. Perspective One-step synthesis of

Tying a knot between crown ethers and porphyrins

• Maksym Matviyishyn and
• Bartosz Szyszko

Beilstein J. Org. Chem. 2023, 19, 1630–1650, doi:10.3762/bjoc.19.120

• notable distinction as they could readily undergo oxidation to yield the corresponding crownphyrins 28–33, incorporating a dipyrrin unit. The synthetic pathway towards crownphyrins is straightforward and relies on a one-pot reaction between diformyldipyrromethane 20a/b and a diamine which introduces the

Synthesis of 7-azabicyclo[4.3.1]decane ring systems from tricarbonyl(tropone)iron via intramolecular Heck reactions

• Aaron H. Shoemaker,
• Elizabeth A. Foker,
• Elena P. Uttaro,
• Sarah K. Beitel and
• Daniel R. Griffith

Beilstein J. Org. Chem. 2023, 19, 1615–1619, doi:10.3762/bjoc.19.118

• amine protection – can potentially take place in one pot). We have shown that this protocol can be applied to the synthesis of several analogs bearing different substitution patterns on the alkene. The structural diversity that can be readily obtained utilizing this chemistry underscores the versatility

Lewis acid-promoted direct synthesis of isoxazole derivatives

• Dengxu Qiu,
• Chenhui Jiang,
• Pan Gao and
• Yu Yuan

Beilstein J. Org. Chem. 2023, 19, 1562–1567, doi:10.3762/bjoc.19.113

• Dengxu Qiu Chenhui Jiang Pan Gao Yu Yuan College of Chemistry and Chemical Engineering, Yangzhou University, Yangzhou 225002, China 10.3762/bjoc.19.113 Abstract Isoxazole derivatives were synthesized via a one-pot method utilizing 2-methylquinoline derivatives as template substrates, sodium

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

• previously been shown in the literature that the first two steps of this Smiles-rearrangement approach can be effectively performed in one pot [49]. Therefore, after allowing the O-alkylation to proceed at room temperature in dimethylethyleneurea (DMEU), we proceeded directly to the hydroxyamides 7 and 8

• through the use of additional NaOH and refluxing the crude alkylation mixture. After heating for 3 h, the desired intermediates were recovered in acceptable yields over this two-step one-pot sequence. The amide hydrolysis of 7 and 8 to the desired free naphthylamines 9 and 10 proved challenging, but was

N-Sulfenylsuccinimide/phthalimide: an alternative sulfenylating reagent in organic transformations

• Fatemeh Doraghi,
• Seyedeh Pegah Aledavoud,
• Mehdi Ghanbarlou,
• Bagher Larijani and
• Mohammad Mahdavi

Beilstein J. Org. Chem. 2023, 19, 1471–1502, doi:10.3762/bjoc.19.106

• the presence of N-(2-bromophenylthio)succinimide 1’ and copper catalyst led to intermolecular sulfenoamination of alkenes and subsequent C–N coupling to produce dihydrobenzothiazine structures 27 in a one-pot manner. Furthermore, deprotection of the amine unit by K2CO3 and Na metal was performed in

Application of N-heterocyclic carbene–Cu(I) complexes as catalysts in organic synthesis: a review

• Nosheen Beig,
• Varsha Goyal and
• Raj K. Bansal

Beilstein J. Org. Chem. 2023, 19, 1408–1442, doi:10.3762/bjoc.19.102

• multifunctional catalytic system 142 incorporating ruthenium nanoparticles (RuNPS) and an NHC–Cu–Cl complex supported on silica (Scheme 56). The catalyst, Ru@SiO2–[Cu(NHC)] was successfully applied to a one-pot tandem A3 reaction of an aldehyde, alkyne, and secondary amine followed by hydrogenation of the

One-pot nucleophilic substitution–double click reactions of biazides leading to functionalized bis(1,2,3-triazole) derivatives

• Hans-Ulrich Reissig and
• Fei Yu

Beilstein J. Org. Chem. 2023, 19, 1399–1407, doi:10.3762/bjoc.19.101

• azide was combined with a subsequent copper-catalyzed (3 + 2) cycloaddition with terminal alkynes. This one-pot process was developed with a simple model alkyne, but then applied to more complex alkynes bearing enantiopure 1,2-oxazinyl substituents. Hence, the precursor compounds 1,2-, 1,3- or 1,4-bis

• the Nobel Prize in 2022 to M. Meldal, K. B. Sharpless and C. R. Bertozzi did not come as a surprise. In most cases the (3 + 2) cycloadditions were performed with isolated (and purified) organic azides, but it was early found that one-pot processes generating the potentially hazardous azides [22] in

• was also discussed in a review article [57] dealing with the various types of bis(1,2,3-triazoles). Since we were not interested in compounds such as 4 we did not further investigate details in order to optimize this process. Instead, we looked at the one-pot nucleophilic substitution to generate

Consecutive four-component synthesis of trisubstituted 3-iodoindoles by an alkynylation–cyclization–iodination–alkylation sequence

• Nadia Ledermann,
• Alae-Eddine Moubsit and
• Thomas J. J. Müller

Beilstein J. Org. Chem. 2023, 19, 1379–1385, doi:10.3762/bjoc.19.99

• electrophilic trapping of the intermediary indole anion with alkyl halides provides a concise one-pot synthesis of 3-iodoindoles. The latter are valuable substrates for Suzuki arylations, which are exemplified with the syntheses of four derivatives, some of them are blue emitters in solution and in the solid

• increasingly interesting [26][27]. In addition, as one-pot processes with a huge exploratory potential and diversity-oriented character, syntheses of indoles by multicomponent reactions have aroused considerable interest [28][29][30]. As part of our program to develop heterocycle syntheses based upon

• Discussion In our previous studies on the alkynylation–cyclization synthesis of 2-substituted (aza)indoles [32][33][34], we could show that the copper-free Pd-catalyzed alkynylation of 2-aminobromopyridines or 2-bromoanilines and the subsequent base-catalyzed anellation in a one-pot fashion proceeds without

Synthesis of ether lipids: natural compounds and analogues

• Marco Antônio G. B. Gomes,
• Alicia Bauduin,
• Chloé Le Roux,
• Romain Fouinneteau,
• Wilfried Berthe,
• Mathieu Berchel,
• Hélène Couthon and
• Paul-Alain Jaffrès

Beilstein J. Org. Chem. 2023, 19, 1299–1369, doi:10.3762/bjoc.19.96

• reacted immediately (one-pot procedure) with sodium borohydride to give 4.4. It must be noted that this sequence does not induce racemization and that 4.4 can be stored for months with 0.5% of solid KOH acting as a stabilizer [72]. Then, 4.4 was alkylated with stearyl tosylate to produce 4.5. The two

• acyl group. Then, the phosphocholine polar head group was introduced with a sequential one-pot procedure using first 2-chloro-2-oxo-1,3,2-dioxaphospholane (12.7) to produce a cyclic phosphate as intermediate that subsequently reacted with trimethylamine to produce thio-PAF 12.8. The opening of

• 22.10. However, the last step features the lower yield (54%) of this 8-step synthesis. In 1994, Bittman et al. reported an alternative strategy to introduce the phosphocholine moiety by the preparation of a cyclic phosphite as a key intermediate [119]. This one-pot three-step sequence starts with the

Unravelling a trichloroacetic acid-catalyzed cascade access to benzo[f]chromeno[2,3-h]quinoxalinoporphyrins

• Chandra Sekhar Tekuri,
• Pargat Singh and
• Mahendra Nath

Beilstein J. Org. Chem. 2023, 19, 1216–1224, doi:10.3762/bjoc.19.89

• Chandra Sekhar Tekuri Pargat Singh Mahendra Nath Department of Chemistry, Faculty of Science, University of Delhi, Delhi 110 007, India 10.3762/bjoc.19.89 Abstract A facile one-pot four-component synthetic methodology is evolved to construct novel copper(II) benzo[f]chromeno[2,3-h

• ; multicomponent synthesis; one-pot reaction; trichloroacetic acid; Introduction π-Conjugated porphyrin macrocycles are known for their applications in numerous areas ranging from oxygen transport, photosynthesis, catalysis and medicine [1][2][3]. In the past several years, diverse organic scaffolds have been

• present study discloses an easy and first synthetic approach to build highly π-conjugated copper(II) benzo[f]chromeno[2,3-h]quinoxalinoporphyrins through a trichloroacetic acid-catalyzed one-pot four-component reaction of 2,3-diamino-5,10,15,20-tetraarylporphyrins, 2-hydroxynaphthalene-1,4-dione, aromatic

Retraction: One-pot odourless synthesis of thioesters via in situ generation of thiobenzoic acids using benzoic anhydrides and thiourea

• Mohammad Abbasi and
• Reza Khalifeh

Beilstein J. Org. Chem. 2023, 19, 1170–1170, doi:10.3762/bjoc.19.85

New one-pot synthesis of 4-arylpyrazolo[3,4-b]pyridin-6-ones based on 5-aminopyrazoles and azlactones

• Vladislav Yu. Shuvalov,
• Ekaterina Yu. Vlasova,
• Tatyana Yu. Zheleznova and
• Alexander S. Fisyuk

Beilstein J. Org. Chem. 2023, 19, 1155–1160, doi:10.3762/bjoc.19.83

• Ave., 55a, 644077 Omsk, Russian Federation 10.3762/bjoc.19.83 Abstract An effective one-pot strategy was developed for the synthesis of 4-arylpyrazolo[3,4-b]pyridin-6-ones from pyrazolo[3,4-b]pyridin-6-ones, obtained by reacting 5-aminopyrazoles with 4-arylidene-2-phenyloxazol-5(4H)-ones (azlactones

• when irradiated with UV light. Keywords: 5-aminopyrazole; azlactone; elimination; fluorescence; one-pot synthesis; pyrazolo[3,4-b]pyridin-6-one; Introduction The pyrazolo[3,4-b]pyridine scaffold is present in many biologically active compounds [1][2][3][4][5][6][7][8][9][10][11][12]. Among them, 4

• carried out as one-pot synthesis, without isolation of the intermediate dihydro derivative 3а. In this case, the solvent (DMSO) could be added at the stage of obtaining dihydro derivative 3a or introduced into the reaction together with t-BuOK. We have explored both variants. When intermediate 3a was

Photoredox catalysis harvesting multiple photon or electrochemical energies

• Mattia Lepori,
• Simon Schmid and
• Joshua P. Barham

Beilstein J. Org. Chem. 2023, 19, 1055–1145, doi:10.3762/bjoc.19.81

• products (e.g., 7) whereas irradiation with blue light (λ = 455 nm) provided disubstituted products 8 (Figure 5A). Additionally, adding a different trapping reagent before switching from green to blue light allows for a sequential and controlled substitution in a one-pot reaction (Figure 5B). 2,4,6

Synthesis of imidazo[4,5-e][1,3]thiazino[2,3-c][1,2,4]triazines via a base-induced rearrangement of functionalized imidazo[4,5-e]thiazolo[2,3-c][1,2,4]triazines

• Dmitry B. Vinogradov,
• Alexei N. Izmest’ev,
• Angelina N. Kravchenko,
• Yuri A. Strelenko and
• Galina A. Gazieva

Beilstein J. Org. Chem. 2023, 19, 1047–1054, doi:10.3762/bjoc.19.80

• hours of reaction. A one-pot method for the synthesis of 1,3-dimethylimidazo[4,5-e][1,3]thiazino[2,3-c][1,2,4]triazine 3a was exemplified by successive reactions of imidazo[4,5-e][1,2,4]triazine 7 with diethyl acetylenedicarboxylate and excess KOH. Acidification of aqueous solutions of potassium salts

Synthesis of tetrahydrofuro[3,2-c]pyridines via Pictet–Spengler reaction

• Elena Y. Mendogralo and
• Maxim G. Uchuskin

Beilstein J. Org. Chem. 2023, 19, 991–997, doi:10.3762/bjoc.19.74

• Elena Y. Mendogralo Maxim G. Uchuskin Perm State University, Bukireva st. 15, Perm, 614990, Russian Federation 10.3762/bjoc.19.74 Abstract A semi-one-pot method for the synthesis of 4-substituted tetrahydrofuro[3,2-c]pyridines by the Pictet–Spengler reaction was developed. The method is based on

• . The reversibility of the acid hydrolysis is quite typical for furans and is more pronounced for di- and polysubstituted furans, due to the higher stability of the latter [49][50][51]. 3-(2-Oxopropyl)piperidin-4-one 5a could be involved into the Paal–Knorr pyrrole synthesis in a one-pot manner. Thus

• methyl iodide (Scheme 5). Conclusion In conclusion, we have developed a semi-one-pot method for the synthesis of 2,3-annulated furans based on the Pictet–Spengler reaction. This method provides a shortcut to 4-substituted tetrahydrofuro[3,2-c]pyridines in reasonable yields starting from readily available

The unique reactivity of 5,6-unsubstituted 1,4-dihydropyridine in the Huisgen 1,4-diploar cycloaddition and formal [2 + 2] cycloaddition

• Xiu-Yu Chen,
• Hui Zheng,
• Ying Han,
• Jing Sun and
• Chao-Guo Yan

Beilstein J. Org. Chem. 2023, 19, 982–990, doi:10.3762/bjoc.19.73

• -fused tetrahydroquinolines (reaction 1 in Scheme 1) [41][42]. Menéndez and co-workers reported a Yb(OTf)3-mediated Povarov reaction of imines and N-alkyl-1,4-dihydropyridines for the synthesis of hexahydrobenzo[h][1,6]naphthyridines (reaction 2 in Scheme 1) [43]. Khan and co-workers employed a one-pot

Aromatic C–H bond functionalization through organocatalyzed asymmetric intermolecular aza-Friedel–Crafts reaction: a recent update

• Anup Biswas

Beilstein J. Org. Chem. 2023, 19, 956–981, doi:10.3762/bjoc.19.72

• reaction between α-naphthol (17) and methyl 2-acetamidoacrylate (18) but promising selectivity was not achieved. The highest enantiomeric excess of 64% was obtained in the presence of P7 as the catalyst (Scheme 6) [30]. In 2018, Reddy and co-workers developed a one pot protocol comprising oxidation and an

• utilizing cyclic N-sulfimines as electrophiles. Aza-Friedel–Crafts reaction involving N-unprotected imino ester as electrophile. Aza-Friedel–Crafts and lactonization cascade. One-pot oxidation and aza-Friedel–Crafts reaction. C1 and C2-symmetric phosphoric acids as catalysts. Aza-Friedel–Crafts reaction

Clauson–Kaas pyrrole synthesis using diverse catalysts: a transition from conventional to greener approach

• Dileep Kumar Singh and
• Rajesh Kumar

Beilstein J. Org. Chem. 2023, 19, 928–955, doi:10.3762/bjoc.19.71

• solvent at 100 °C (Scheme 6). Finally, compounds 13 were used to prepare various arylpyrrolo- and pyrazolopyrrolizinones for diverse biological activity. In 2007, Török and co-workers [60] reported a convenient one-pot synthesis of N-sulfonyl-substituted pyrroles, indoles, and carbazole via a modified

• and forms an unstable intermediate that easily forms activated dialdehyde B. The amine 24 reacts with activated dialdehyde and provides the corresponding pyrrole 25 through the removal of water molecules. Smith and co-workers [65] reported a modified one-pot, two-step Clauson–Kaas procedure for the

Asymmetric tandem conjugate addition and reaction with carbocations on acylimidazole Michael acceptors

• Brigita Mudráková,
• Renata Marcia de Figueiredo,
• Jean-Marc Campagne and
• Radovan Šebesta

Beilstein J. Org. Chem. 2023, 19, 881–888, doi:10.3762/bjoc.19.65

• intermediates among other metal enolates obtained in conjugate additions. Experimental General procedure for the one-pot conjugate addition of organozinc reagents to acylimidazole followed by trapping with carbocations: In a flame-dried Schlenk flask flushed with Ar, Cu(OTf)2 (1.81 mg, 0.005 mmol, 2 mol %) and

Synthesis of substituted 8H-benzo[h]pyrano[2,3-f]quinazolin-8-ones via photochemical 6π-electrocyclization of pyrimidines containing an allomaltol fragment

• Constantine V. Milyutin,
• Andrey N. Komogortsev,
• Boris V. Lichitsky,
• Mikhail E. Minyaev and
• Valeriya G. Melekhina

Beilstein J. Org. Chem. 2023, 19, 778–788, doi:10.3762/bjoc.19.58

• Scheme S5 in Supporting Information File 1). Based on the obtained results, we have developed a preparative telescopic method for the synthesis of polycycles 12. The presented two-step one-pot approach includes the preliminary photoconversion of the starting pyrimidines 9 in DMF to the corresponding

• derivatives are stable products and do not convert into polyaromatic benzo[h]pyrano[2,3-f]quinazolines upon further UV irradiation. The structures of two of the dihydrobenzo[h]pyrano[2,3-f]quinazolines were confirmed by X-ray diffraction analysis. Based on the obtained results, a two-step one-pot protocol for

Sulfate radical anion-induced benzylic oxidation of N-(arylsulfonyl)benzylamines to N-arylsulfonylimines

• Joydev K. Laha,
• Pankaj Gupta and
• Amitava Hazra

Beilstein J. Org. Chem. 2023, 19, 771–777, doi:10.3762/bjoc.19.57

• synthesis of synthetically useful N-arylsulfonylimines from N-(arylsulfonyl)benzylamines using K2S2O8 in the presence of pyridine as a base is reported herein. In addition, a “one-pot” tandem synthesis of pharmaceutically relevant N-heterocycles by the reaction of N-arylsulfonylimines, generated in situ

• approach, a gram-scale synthesis and a “one-pot” tandem synthesis of pharmaceutically relevant N-heterocycles by the reaction of in situ-generated N-arylsulfonylimines with various ortho-substituted anilines were also developed. The mechanism of the oxidation is believed to occur via hydrogen atom

• synthetic utility of the developed protocol, a tandem “one-pot” synthesis of N-heterocycles was successfully executed (Scheme 3). Thus, exposition of substrates 1 under the optimized reaction conditions followed by the addition of ortho-substituted anilines 3 and K2S2O8 (1 equiv) and heating the reaction

Construction of hexabenzocoronene-based chiral nanographenes

• Ranran Li,
• Di Wang,
• Shengtao Li and
• Peng An

Beilstein J. Org. Chem. 2023, 19, 736–751, doi:10.3762/bjoc.19.54

• . Meanwhile, this NG 70 can also be synthesized from compound 68 through oxidative cyclodehydrognation and dimerization in one pot. The isomerization barrier was determined as over 35 kcal/mol at 170 °C, and 37 kcal/mol by DFT calculation, indicating a high degree of optical stability of pure enantiomers [51

Synthesis of imidazo[1,2-a]pyridine-containing peptidomimetics by tandem of Groebke–Blackburn–Bienaymé and Ugi reactions

• Oleksandr V. Kolomiiets,
• Alexander V. Tsygankov,
• Maryna N. Kornet,
• Aleksander A. Brazhko,
• Vladimir I. Musatov and
• Valentyn A. Chebanov

Beilstein J. Org. Chem. 2023, 19, 727–735, doi:10.3762/bjoc.19.53

• proved to be inefficient. In addition, we also tested the one-pot method for the synthesis of similar structures [32]. Aminopyridine, aldehyde and Sc(OTf)3 as catalyst were stirred in MeOH/DCM for 45 min at room temperature, then the isocyanide was added and the mixture was stirred for another 8 h

Strategies in the synthesis of dibenzo[b,f]heteropines

• David I. H. Maier,
• Barend C. B. Bezuidenhoudt and
• Charlene Marais

Beilstein J. Org. Chem. 2023, 19, 700–718, doi:10.3762/bjoc.19.51

• , whereafter Buchwald–Hartwig amination afford the various diarylazepines. A three-component one-pot process allowed for a second in situ Buchwald–Hartwig amination of the diarylazepine with aryl or benzyl halides to give the respective N-aryl and N-benzylazepine derivatives 83 and 84 (Scheme 16). 3.2 Mizoroki

• dibenzoazepines 62. Double Buchwald–Hartwig amination towards 10,11-dihydro-5H-dibenzo[b,f]azepine derivatives 71. One-pot Suzuki coupling–Buchwald–Hartwig amination. One-pot Rh/Pd-catalysed synthesis of dihydropyridobenzazepines. A retrosynthetic pathway to dibenzo[b,f]azepines via Mizoroki–Heck reaction. One

• -pot domino Pd-catalyzed Mizoroki–Heck–Buchwald–Hartwig synthesis of dibenzo[b,f]azepines. Dibenzo[b,f]thiapine and -oxepine synthesis via SNAr (thio)etherification, Wittig methylenation and Mizoroki–Heck reaction. A retrosynthetic pathway to dibenzo[b,f]oxepines via Ullmann coupling. Ullmann-type