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Search for "domino reactions" in Full Text gives 57 result(s) in Beilstein Journal of Organic Chemistry.
Catalytic multi-step domino and one-pot reactions
Beilstein J. Org. Chem. 2024, 20, 254–256, doi:10.3762/bjoc.20.25
- Svetlana B. Tsogoeva Department of Chemistry and Pharmacy, Organic Chemistry Chair I and Interdisciplinary Center for Molecular Materials (ICMM), Friedrich-Alexander-Universität Erlangen-Nürnberg, Nikolaus Fiebiger-Straße 10, 91058 Erlangen, Germany 10.3762/bjoc.20.25 Keywords: domino reactions
- simple compounds. In particular, catalytic domino reactions and one-pot processes with excellent selectivity and functional-group tolerance are of significant interest to industrial and academic research. In the so-called domino reactions, all of the required reagents, the catalyst, and a solvent are
- steps, which is superior to conventional organic synthesis. The Thematic Issue “Catalytic multi-step domino and one-pot reactions” in the Beilstein Journal of Organic Chemistry, which I had the pleasure to edit, covers the recent strategies of domino reactions and one-pot syntheses and presents the
Selective construction of dispiro[indoline-3,2'-quinoline-3',3''-indoline] and dispiro[indoline-3,2'-pyrrole-3',3''-indoline] via three-component reaction
Beilstein J. Org. Chem. 2023, 19, 1234–1242, doi:10.3762/bjoc.19.91
- as Michael acceptors, 1,3-dipolarophiles, 1,4-dienophiles and other multiple substrates. They have been widely employed as key component to finish many multicomponent and domino reactions [26][27][28][29][30][31][32][33][34][35]. Recently, the Michael adduct of 3-methyleneoxindoles with various
- nucleophiles, especially active methylene compounds, have attracted much attentions [36][37][38][39][40][41]. This kind of Michael adduct has more than one reactive site and could proceed domino reactions with various electrophiles [42][43][44][45][46][47][48][49]. In this respect, several elegant domino or
The unique reactivity of 5,6-unsubstituted 1,4-dihydropyridine in the Huisgen 1,4-diploar cycloaddition and formal [2 + 2] cycloaddition
Beilstein J. Org. Chem. 2023, 19, 982–990, doi:10.3762/bjoc.19.73
- reactions [16][17][18][19][20][21][22][23][24][25]. Recently, much attention has been devoted to the development of new domino reactions containing reactive Huisgen 1,4-dipoles as key components for the assembly of many biologically important nitrogen-containing six-membered heterocyclic compounds [26][27
- as one of the most valuable synthons to construct diverse carbocyclic and heterocyclic systems as well as many open-chain compounds [9][10][11][12][13][14][15]. In recent years, in situ generated Huisgen 1,4-dipoles were also widely employed to design highly efficient multicomponent and domino
Enolates ambushed – asymmetric tandem conjugate addition and subsequent enolate trapping with conventional and less traditional electrophiles
Beilstein J. Org. Chem. 2023, 19, 593–634, doi:10.3762/bjoc.19.44
- , crop-protecting agents, or advanced materials. Their syntheses often involve numerous reaction steps requiring laborious isolation and intermediate product purification steps. An important strategy for improving syntheses’ effectiveness is the concept of domino reactions, cascade, or tandem reactions
- asymmetric conjugate addition. The magnesium enolates 56 then participated in a copper(II)-mediated intramolecular oxidative coupling to afford benzofused spirocyclic cycloalkanones 57 (Scheme 14) [45]. Our team became interested in domino reactions of metal enolates generated by Cu-catalyzed asymmetric
- (Scheme 16). Within the framework of these domino reactions, we have mainly employed ferrocenyl phosphane ligands such as Taniaphos or Josiphos. In collaboration with Prof. Schmalz from Cologne University, we have also tested phosphite-phosphine ligands (e.g., L15) from their lab. The advantage of these
Transition-metal-catalyzed domino reactions of strained bicyclic alkenes
Beilstein J. Org. Chem. 2023, 19, 487–540, doi:10.3762/bjoc.19.38
- -catalyzed domino reactions of strained bicyclic alkenes, including both homo- and heterobicyclic alkenes. These compounds are important synthons in organic synthesis, providing an important platform for the construction of biologically/medicinally significant compounds which bear multiple stereocenters. The
- on the functionalization of the bicyclic framework itself rather than its use as a transient mediator for domino reactions [13][14][15][16][17]; however, we point the reader to several excellent reviews. The “trapped” alkyl metal intermediate can undergo subsequent migratory insertion steps with
- . Throughout the past decade, research efforts have demonstrated a broad range of strained bicyclic alkenes can be exploited in domino reactions to selectively generate highly functionalized ring systems. Over the years, several different metal catalysts have been used, each allowing for a breadth of unique
Molecular diversity of the base-promoted reaction of phenacylmalononitriles with dialkyl but-2-ynedioates
Beilstein J. Org. Chem. 2022, 18, 991–998, doi:10.3762/bjoc.18.99
- -carboxamides with unprecedented rearrangement of the alkyl group [34] (reaction 4 in Scheme 1). Inspired by these novel reactions and in continuation of our aim to develop domino reactions of electron-deficient alkynes [35][36][37][38][39][40][41][42][43][44][45][46][47][48][49][50], we have investigated the
Tri(n-butyl)phosphine-promoted domino reaction for the efficient construction of spiro[cyclohexane-1,3'-indolines] and spiro[indoline-3,2'-furan-3',3''-indolines]
Beilstein J. Org. Chem. 2022, 18, 669–679, doi:10.3762/bjoc.18.68
- respect, we have also developed several domino reactions by employing tertiary phosphine addition to electron-deficient alkynes as key protocol for the construction of diverse polycyclic spirooxindoles [53][54][55][56][57][58][59]. In continuation of our aim to explore elegant domino reactions for spiro
Menadione: a platform and a target to valuable compounds synthesis
Beilstein J. Org. Chem. 2022, 18, 381–419, doi:10.3762/bjoc.18.43
- , contributing significantly to the progress of the synthesis studies in aqueous medium. The Diels–Alder reaction using menadione (10) was also studied by Bendiabdellah and co-workers, who reported the intramolecular Diels–Alder domino reactions promoted by Lewis acids [110]. The reaction involving menadione (10
Iron-catalyzed domino coupling reactions of π-systems
Beilstein J. Org. Chem. 2021, 17, 2848–2893, doi:10.3762/bjoc.17.196
- substantial improvements in efficient synthesis because of domino reactions. These protocols are more atom-economic, produce less waste, and demand less time compared to a classical stepwise reaction. Although iron-catalyzed domino reactions require a mindset that differs from the more routine noble-metal
- the design of novel domino reactions. Keywords: cascade; catalysis; coupling; earth-abundant; iron; Introduction Over the past couple decades, the use of transition-metal-catalyzed cross-coupling reactions have become a staple within the organic chemist’s arsenal of carbon–carbon and carbon
- to the breadth of reactions viable from iminyl radicals, generating through the homolytic cleavage of the N–O bond, a number of Fe-catalyzed domino reactions have been investigated. In 2018, Okamoto and Ohe reported an iminoarylation of γ,δ-unsaturated oxime esters 165 with arenes 166 (Scheme 35
Efficient synthesis of polyfunctionalized carbazoles and pyrrolo[3,4-c]carbazoles via domino Diels–Alder reaction
Beilstein J. Org. Chem. 2021, 17, 2425–2432, doi:10.3762/bjoc.17.159
- efficient domino reactions for the synthesis of biologically important carbazole derivatives [48][49][50][51][52][53], herein we wish to report the DDQ-mediated dehydrogenative Diels–Alder reaction of 3-(indol-3-yl)maleimides and benzoyl-substituted 3-ethylindoles with readily available chalcones for the
Synthesis of 1-indolyl-3,5,8-substituted γ-carbolines: one-pot solvent-free protocol and biological evaluation
Beilstein J. Org. Chem. 2021, 17, 1453–1463, doi:10.3762/bjoc.17.101
- for the design of efficient one-step transformations for complex molecule synthesis [23][24]. Employing domino reactions to simplify cumbersome industrial processes can afford complex pharmaceutical products in an economical and environment-friendly manner [25]. Easy workup procedures and single-step
Unexpected one-pot formation of the 1H-6a,8a-epiminotricyclopenta[a,c,e][8]annulene system from cyclopentanone, ammonia and dimethyl fumarate. Synthesis of highly strained polycyclic nitroxide and EPR study
Beilstein J. Org. Chem. 2019, 15, 2664–2670, doi:10.3762/bjoc.15.259
- to the N–O· group. Keywords: domino reactions; EPR; nitroxide; spin relaxation; Introduction Domino reactions have attracted much attention as an approach for the synthesis of complex molecules in a few steps [1]. The utility of multicomponent reactions involving amines, activated olefins and
Novel (2-amino-4-arylimidazolyl)propanoic acids and pyrrolo[1,2-c]imidazoles via the domino reactions of 2-amino-4-arylimidazoles with carbonyl and methylene active compounds
Beilstein J. Org. Chem. 2019, 15, 1032–1045, doi:10.3762/bjoc.15.101
- the formation of both unexplored heterocyclic systems containing a free amino group open for chemical modifications and the corresponding hetarylpropanoic acids providing useful templates for the synthesis of some marine alkaloids or their analogues. In domino reactions of the 2-amino-4-arylimidazoles
Efficient synthesis of pyrazolopyridines containing a chromane backbone through domino reaction
Beilstein J. Org. Chem. 2019, 15, 874–880, doi:10.3762/bjoc.15.85
- new fused heterocyclic backbones has always been a major challenge in the field of organic synthesis [1][2][3]. Multicomponent reactions (MCRs) and domino reactions are known as efficient synthetic approaches for the synthesis of complex molecules [4][5][6]. Domino reactions have been defined by
- Tietze and were applied for the synthesis of complicated scaffolds [7][8][9]. The selection of a suitable starting material and designing a post-transformational reaction is a key point for the synthesis of complex molecules through the designing of domino reactions [10]. Chromone derivatives have been
An efficient synthesis of the guaiane sesquiterpene (−)-isoguaiene by domino metathesis
Beilstein J. Org. Chem. 2019, 15, 858–862, doi:10.3762/bjoc.15.83
- (−)-Isoguaiene was prepared from (S)-citronellal in only 9–10 steps with good overall yields. Either a trienyne or a dienediyne metathesis and highly diastereoselective organocatalytic Michael additions of aldehydes derived from (S)-citronellal served as the key transformations. Keywords: domino reactions
Annulation of 1H-pyrrole-2,3-diones by thioacetamide: an approach to 5-azaisatins
Beilstein J. Org. Chem. 2019, 15, 364–370, doi:10.3762/bjoc.15.32
- developed via an unprecedented annulation of pyrrolo[2,1-c][1,4]benzoxazine-1,2,4-triones by thioacetamide. A new way of C–H functionalization of thioacetamide has been discovered. The reaction proceeds under green catalyst-free conditions. Keywords: annulation; domino reactions; isatin; nitrogen
A novel and efficient synthesis of phenanthrene derivatives via palladium/norbornadiene-catalyzed domino one-pot reaction
Beilstein J. Org. Chem. 2019, 15, 291–298, doi:10.3762/bjoc.15.26
- this approach had low reactivity, which needed higher reaction temperatures and longer reaction time. Therefore, the development of novel, efficient, and highly functional group tolerant methods for the synthesis of phenanthrene derivatives is still desirable. Domino reactions such as norbornene
Mn-mediated sequential three-component domino Knoevenagel/cyclization/Michael addition/oxidative cyclization reaction towards annulated imidazo[1,2-a]pyridines
Beilstein J. Org. Chem. 2018, 14, 3078–3087, doi:10.3762/bjoc.14.287
- proceeds through a domino Knoevenagel/cyclization/Michael addition/oxidative cyclization reaction sequence. Keywords: 2-aminochromene; domino reaction; imidazo[1,2-a]pyridine; 2-iminochromene; Michael addition; multicomponent reaction; oxidation; pyridine amination; Introduction Domino reactions are well
- given to domino reactions with an oxidation step, revealing possibilities for shifting the equilibrium by making products more stable or in situ generating reactive intermediates [2][3][4][5][6][7][8][9][10][11][12][13]. In its turn, multicomponent reactions (MCRs), usually occurring as domino processes
One-pot synthesis of epoxides from benzyl alcohols and aldehydes
Beilstein J. Org. Chem. 2018, 14, 2308–2312, doi:10.3762/bjoc.14.205
- into carbonyls [8][9][10][11][12][13][14][15][16][17], and application to cascade or domino reactions [18][19]. More recently, our group has used benzyl epoxides for the photoredox generation of carbonyl ylides which are leveraged in the synthesis of cyclic ethers [20]. This work has led us to search
Hypervalent organoiodine compounds: from reagents to valuable building blocks in synthesis
Beilstein J. Org. Chem. 2018, 14, 1508–1528, doi:10.3762/bjoc.14.128
- . Several elegant catalytic domino reactions, accordingly, have been recently designed to incorporate both aryl groups into the products. Cyclic diaryl-λ3-iodanes Cyclic diaryl-λ3-iodanes have been extensively studied for the preparation of complex polycyclic structures following the application of
- catalytic domino reactions. The group of Hayashi has reported in 2004 the first example of the transformation of a cyclic diaryl-λ3-iodane, for which both Ar–I bonds are used in a palladium cross-coupling reaction [56]. It relies on a double Heck reaction performed with methyl vinyl ketone in the presence
Synthesis of chiral 3-substituted 3-amino-2-oxindoles through enantioselective catalytic nucleophilic additions to isatin imines
Beilstein J. Org. Chem. 2018, 14, 1349–1369, doi:10.3762/bjoc.14.114
- –Hillman reactions, Friedel–Crafts reactions, aza-Henry reactions, domino reactions initiated by nucleophilic additions to isatin imines, and miscellaneous reactions. Most of the reactions depicted in this review have been promoted by a wide variety of chiral organocatalysts but chiral metal catalysts have
- isatin imine (81% yield, 86% ee with R1 = Me, R2 = H). Domino reactions In the last decade, a number of highly enantioselective domino processes [72][73][74] catalyzed by either chiral organocatalysts [26] or chiral metals have been published [75][76][77]. In 2016, Li and Li reported an efficient
- reactions, aza-Morita–Baylis–Hilman reactions, Friedel–Crafts reactions, aza-Henry reactions, domino reactions, among others have allowed a wide range of these biologically important chiral products to be achieved in generally excellent enantioselectivities and high yields by using different types of metal
Methyl isocyanide as a convertible functional group for the synthesis of spirocyclic oxindole γ-lactams via post-Ugi-4CR/transamidation/cyclization in a one-pot, three-step sequence
Beilstein J. Org. Chem. 2018, 14, 875–883, doi:10.3762/bjoc.14.74
- ]. Significant efforts have been made to design creative synthetic strategies for spirocyclic oxindole molecules, of which, isatin-based domino reactions [24][25][26][27][28][29][30] have proved to be very versatile [31] and readily achievable [32][33][34][35][36][37]. However, finding a simple and efficient
An air-stable bisboron complex: a practical bidentate Lewis acid catalyst
Beilstein J. Org. Chem. 2018, 14, 618–625, doi:10.3762/bjoc.14.48
- LUMOs are rather high in energy [9][10][11][12]. In the past years, we demonstrated a bisboron bidentate Lewis acid (Scheme 1, A) as an efficient catalyst for the IEDDA reaction of 1,2-diazines to access 1,2-substituted aromatics [13][14]. Additionally, we could incorporate this reactivity in domino
- reactions combining the IEDDA step with rearrangements [15] or additional Diels–Alder reactions [16]. However, the methodology requires an air and moisture-sensitive bisboron catalyst. The preparation as well as the handling requires special equipment such as a glovebox, therefore, restricting its
Rh(II)-mediated domino [4 + 1]-annulation of α-cyanothioacetamides using diazoesters: A new entry for the synthesis of multisubstituted thiophenes
Beilstein J. Org. Chem. 2017, 13, 2569–2576, doi:10.3762/bjoc.13.253
- domino reactions of diazo compounds with intermediate formation of ylides [7][8][9][10][11][12][13][14][15][16][17][18][19][20][21]. Thus, it was for example shown that ammonium or oxonium ylides generated in the course of intermolecular processes can be easily trapped by ketones, imines, α,β-unsaturated
- ]. Conclusion In summary, the investigation of Rh(II)-catalyzed domino reactions of acyclic diazoesters with α-cyanothioacetamides lead to elaboration of a new approach for the synthesis of multisubstituted thiophenes. These reactions could be applied for the preparation of 5-amino-3-(alkoxycarbonylamino
- Str., 620002, Ekaterinburg, Russia Center for X-ray Diffraction Studies, St-Petersburg State University, 26 University pr., 198504, Saint-Petersburg, Russia 10.3762/bjoc.13.253 Abstract A new approach towards the synthesis of multisubstituted thiophenes is elaborated based on Rh(II)-catalyzed domino
One-pot syntheses of blue-luminescent 4-aryl-1H-benzo[f]isoindole-1,3(2H)-diones by T3P® activation of 3-arylpropiolic acids
Beilstein J. Org. Chem. 2017, 13, 2340–2351, doi:10.3762/bjoc.13.231
- -emitting diodes (OLEDs) [2][3][4][5]. As a consequence efficient and efficacious syntheses of fluorescent molecules can be most advantageously addressed by diversity-oriented syntheses [6][7][8], namely by multicomponent [9][10][11][12][13][14][15][16][17][18][19][20][21] and domino reactions [22][23][24
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