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Search for "domino" in Full Text gives 178 result(s) in Beilstein Journal of Organic Chemistry.
Steroid diversification by multicomponent reactions
Beilstein J. Org. Chem. 2019, 15, 1236–1256, doi:10.3762/bjoc.15.121
- nitrogen atom in their nucleus) [53][54]. This strategy employs domino Knoevenagel/hetero-Diels–Alder procedures for the assembly of such steroid mimics. However, we have decided not to include it in this review because several book chapters and reviews have already covered this chemistry [55][56]. 4
Switchable selectivity in Pd-catalyzed [3 + 2] annulations of γ-oxy-2-cycloalkenones with 3-oxoglutarates: C–C/C–C vs C–C/O–C bond formation
Beilstein J. Org. Chem. 2019, 15, 1107–1115, doi:10.3762/bjoc.15.107
- -2-cycloalkenones, simply differing on the reaction temperature, are disclosed. These domino transformations allow C–C/O–C or C–C/C–C [3 + 2] annulations at will, via an intermolecular Pd-catalyzed C-allylation/intramolecular O- or C-1,4-addition sequence, respectively. In particular, exploiting the
- past decades, palladium chemistry has gained an important place in the toolbox of chemists, and its use became a privileged strategy for the selective formation of carbon–carbon and carbon–heteroatom bonds [2][3][4][5]. Among the different types of palladium-catalyzed transformations, domino – alias
- long-term project dedicated to domino sequences [16][17][18][19][20][21][22] and Pd-catalyzed transformations [23][24][25][26][27][28][29][30], we recently reported a Pd(0)-catalyzed synthesis of bi- and tricyclic structures incorporating pyrrolidone rings (Scheme 1) [31]. In this transformation
Multicomponent reactions (MCRs): a useful access to the synthesis of benzo-fused γ-lactams
Beilstein J. Org. Chem. 2019, 15, 1065–1085, doi:10.3762/bjoc.15.104
- structure. Those starting materials must be added all together in the reaction container and, therefore, other approaches [67][68][69] featuring sequential (domino, tandem or cascade) [70][71] reactions, where one intermediate is initially preformed before additional reagents are added, are not included in
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
- base led to a fused chromanyl-cyanopyridine. High selectivity, high atom economy, and good to high yields in addition to mild reaction conditions are the advantages of this approach. Keywords: chromane; domino reaction; fused heterocyclic skeletons; pyrazolopyridines; Introduction The synthesis of
- 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
- feature a domino metathesis event and an organocatalytic Michael addition as the key steps. In closer analogy to our improved synthesis of clavukerin A (2) [8], a relay metathesis [9] of trienyne 3 was expected to lead to the hydroazulene 1 selectively. Trienyne 3 was envisioned to result from a
- required to effect the relay metathesis of 3 to (−)-isoguaiene (1) in refluxing benzene in a good yield of 51%. Thus, by application of a domino metathesis strategy featuring trienyne 3, only 9 steps were needed to secure the guaiane sesquiterpene 1 in 19.7% overall yield starting from (S)-citronellal (5
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
- alkynylation for the aryl iodides. In this paper, we developed an efficient domino reaction of aryl iodides with ortho-bromobenzoyl chlorides and norbornadiene leading to phenanthrene derivatives, which could be widely used in the synthesis of vital intermediates for functional materials, pharmaceutical agents
- compound z-6 was isolated in 88% yield. Based on the above experimental results and the use of norbornadiene in Catellani reactions followed by retro-Diels–Alder reaction firstly reported by Lautens et al. [22][23][24], which is mentioned in recent works [11], a proposed mechanism for this domino reaction
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
- recognized for their ability to effectively synthesize organic compounds, as far as creating two and more chemical bonds in one-step decreases waste, resources and time, and makes the development of methodology of synthesis in a domino fashion a substantial task [1]. Recently, much attention in research was
- 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
Synthesis of indole–cycloalkyl[b]pyridine hybrids via a four-component six-step tandem process
Beilstein J. Org. Chem. 2018, 14, 2907–2915, doi:10.3762/bjoc.14.269
- -yl)-3-oxopropanenitrile; tandem reaction; Introduction The syntheses of novel heterocycles through greener protocols have received a great deal of attention of the synthetic organic chemists in view of environmental concerns [1][2][3]. The multicomponent tandem/domino reaction is one among several
- -oxopropanenitriles, aromatic aldehydes, cycloalkanones and ammonium acetate. This work also stems from our continuous effort in synthesizing novel cycloalkyl[b]pyridine-3-carbonitrile hybrid heterocycles via tandem/domino reaction [71][72]. Results and Discussion Initially the precursors viz. 3-(1H-indol-3-yl)-3
Domino ring-opening–ring-closing enyne metathesis vs enyne metathesis of norbornene derivatives with alkynyl side chains. Construction of condensed polycarbocycles
Beilstein J. Org. Chem. 2018, 14, 2708–2714, doi:10.3762/bjoc.14.248
- investigated with the objective of constructing condensed polycyclic structures. This investigation demonstrated that the generally observed domino reaction course involving a ring-opening metathesis of the norbornene unit and a ring-closing enyne metathesis is influenced to a great extent by the nature of the
- functional group and the substrate structure and may follow a different reaction course than what is usually observed. In cases where ROM–RCEYM occurred, the resulting 1,3-diene reacts in situ with the dienophile to provide condensed tetracyclic systems. Keywords: Diels–Alder reaction; domino process; enyne
- metathesis; natural products; polycarbocycles; Introduction The metathesis of norbornene derivatives having an alkene side-chain on the norbornene nucleus with Grubbs’ ruthenium catalysts has been extensively investigated. Generally the reaction proceeds through a domino process involving a ring opening of
Synthesis of functionalised β-keto amides by aminoacylation/domino fragmentation of β-enamino amides
Beilstein J. Org. Chem. 2018, 14, 2602–2606, doi:10.3762/bjoc.14.238
- -protected amino acids. Domino fragmentation of the obtained intermediates leads to functionalised β-keto amides, bearing a protected amino group in their side chain. Keywords: amino acids; C-acylation; domino reaction; enamines; enaminones; keto amides; retro-Mannich; Introduction The acylation of amide
- (4) intermediates were successfully prepared, we proceeded with the removal of the Boc protection group from the ethylenediamine moiety in order to trigger the domino fragmentation to the targeted β-keto amides. In the course of these experiments the two series of compounds showed markedly different
- behaviour. Domino fragmentation of α-aminoacyl intermediates 3 to N-protected γ-amino-β-ketoamides 5 Initially we tried a procedure developed earlier by us for simpler β-keto amides (30 min in neat TFA, then aqueous NaOAc) [22]. In contrast to the preparation of non-functionalised β-keto amides, here these
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
- domino process for the introduction of both aromatic rings of diaryl-λ3-iodanes, though a small excess of this reagent is needed to obtain good yields. An initial N-arylation reaction of 3,5-dimethylpyrazole is performed in the presence of potassium carbonate, in xylene at 70 °C, releasing 1 equivalent
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
- asymmetric formal [3 + 2] annulation reaction between N-Boc-isatin imines 3 and 1,4-dithiane-2,5-diol (53) as equal equivalent of 2-mercaptoacetaldehyde [78]. The domino reaction catalyzed by chiral tertiary amine-squaramide catalyst 54 began with the addition of 2-mercaptoacetaldehyde to isatin imine 3
Atom-economical group-transfer reactions with hypervalent iodine compounds
Beilstein J. Org. Chem. 2018, 14, 1263–1280, doi:10.3762/bjoc.14.108
- only one equivalent of the iodane 1a would have been sufficient. In recent years a variety of domino C–H and/or N–H arylations as powerful tools towards selective diarylations of (hetero)arenes was employed by Greaney and co-workers, who were among the first to establish more atom-economical procedures
- organic electronics and can be obtained in good yields and an AE of 48% (Ar1 = p-Tol, Ar2 = Ar3 = Ph) using this Cu(I)-catalysed domino approach. The formation of an intermediately found diarylaniline supposedly follows a Cu(I)/Cu(III) cycle, whereas a radical mechanism is proposed for the second
- dithiocarbamates 7 and 7’ from one equivalent of diaryliodonium salt 1. Synthesis of substituted isoindolin-1-ones 9 from 2-formylbenzonitrile 8 and the postulated reaction mechanism. Domino C-/N-arylation of indoles 10. Domino modification of N-heterocycles 12 via in situ-generated directing groups. Synthesis of
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
- spiro[indoline-3,2'-pyrrolidine]-2,5'-diones, via a post-Ugi-domino transamidation/cyclization sequential process, has been achieved in three sequential steps utilizing a one-pot reaction protocol. The variation in carboxylic acid substrates allows for the generation of new chiral racemic quaternary
- economical, simple and generate ample molecular diversity with the ease of using readily available starting materials. Developing new, post-modified Ugi-four-component reaction (Ugi-4CR) transformations in domino cyclization [12][13][14][15] sequences are very important for achieving unprecedented chemical
- ]. 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
Recent developments in the asymmetric Reformatsky-type reaction
Beilstein J. Org. Chem. 2018, 14, 325–344, doi:10.3762/bjoc.14.21
- halofluoroacetate. When the opposite enantiomer of the ligand (1S,2R)-59 was used under the same reaction conditions, it provided the corresponding (3R,4S) product 62a in 70% yield and 90% ee starting from the corresponding imine 60a (Scheme 23). Unfortunately, the scope of this domino Reformatsky/cyclization
- (Scheme 23). As an extension of the precedent methodology, the same ligand (1R,2S)-59 was applied to promote the enantioselective domino aza-Reformatsky/cyclization reaction of aromatic imines 60a–h with ethyl bromodifluoroacetate (26) [48]. In this case, a stoichiometric amount of this ligand was
- a stoichiometric amount of a chiral 1,2-amino alcohol ligand [45]. Reformatsky reaction of aldehydes with an enolate equivalent prepared from phenyl isocyanate and CH2(ZnI)2 performed in the presence of a chiral diarylprolinol ligand [46]. Domino aza-Reformatsky/cyclization reactions of imines with
5-Aminopyrazole as precursor in design and synthesis of fused pyrazoloazines
Beilstein J. Org. Chem. 2018, 14, 203–242, doi:10.3762/bjoc.14.15
- shape of compound 93 makes it chiral in nature. It was proposed that there is in situ oxidation of ethanol to ethanal by conc. HNO3 which turned the reaction into a multi-component domino assembly of reactants hydrazine 14, β-ketonitriles 15 and acetaldehyde. Rahmati [75] carried out a reaction of 5
- domino reaction of 5-aminopyrazoles 16, cyclic 1,3-diones 58 and arylglyoxals 98 under microwave irradiation. Triethylamine (20 mol %) as base and DMSO as solvent at 120 °C provided best results with high yields of pyrazolo[3,4-e]indolizines (a derivative of pyrazolo[3,4-b]pyridines) 102 (Scheme 30
Ring-size-selective construction of fluorine-containing carbocycles via intramolecular iodoarylation of 1,1-difluoro-1-alkenes
Beilstein J. Org. Chem. 2017, 13, 2682–2689, doi:10.3762/bjoc.13.266
- latter case, the domino-Friedel–Crafts-type cyclization proceeded via the cleavage of two carbon–fluorine bonds to afford polycyclic aromatic hydrocarbons [15][16][17][18][19][20][21]. Both types of cationic cyclization proceeded exclusively at the carbon atoms α to the fluorine substituents, because the
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
- 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
- was also shown that α-cyanothioacetamides easily interact with dirhodium carboxylates to give rather stable 2:1 complexes, resulting in an evident decrease in the efficiency of the catalytic process at moderate temperatures (20–30 °C). Keywords: [4 + 1]-annulation; catalysis; diazo compounds; domino
- 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
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
- Düsseldorf, Universitätsstraße 1, D-40225 Düsseldorf, Germany 10.3762/bjoc.13.231 Abstract In situ activation of 3-arylpropiolic acids with T3P® (n-propylphosphonic acid anhydride) initiates a domino reaction furnishing 4-arylnaphtho[2,3-c]furan-1,3-diones in excellent yields. Upon employing these
- -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
- -arylnaphtho[2,3-c]furan-1,3-diones and 4-aryl-1H-benzo[f]isoindole-1,3(2H)-diones Starting from phenylpropiolic acids 1 we first set out to optimize the reaction conditions for the domino synthesis of the 4-arylnaphtho[2,3-c]furan-1,3-diones 2a and 2b with T3P® as an activating agent, varying temperature and
Dialkyl dicyanofumarates and dicyanomaleates as versatile building blocks for synthetic organic chemistry and mechanistic studies
Beilstein J. Org. Chem. 2017, 13, 2235–2251, doi:10.3762/bjoc.13.221
- perhydroquinoxaline derivative 73. Synthesis of ethyl 7-aminopteridin-6-carboxylates 75 via a domino reaction. Synthesis of morhpolin-2-ones 80 from E-1 and β-aminoalcohols 78 through an initial aza-Michael addition and subsequent heterocyclization step. Reaction of 3-amino-5-arylpyrazoles 81 with dialkyl
Conjugated nitrosoalkenes as Michael acceptors in carbon–carbon bond forming reactions: a review and perspective
Beilstein J. Org. Chem. 2017, 13, 2214–2234, doi:10.3762/bjoc.13.220
- reagents; (3) the elaboration of tandem and domino-processes utilizing conjugate addition of C-nucleophiles to nitrosoalkenes and finally, (4) the design of catalytic enantioselective versions of the Michael addition to nitrosoalkenes (for advances in catalytic asymmetric cycloadditions of nitrosoalkenes
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