One-pot multicomponent synthesis

A family of interesting polycychc systems 106 related to pyrrolidines was obtained in a one-pot double intermolecular 1,3-dipolar cycloaddition, irradiating derivatives of o-allyl-sahcylaldehydes with microwaves in toluene for 10 min in presence of the TEA salt of glycine esters [71]. A very similar approach was previously proposed by Bashiardes and co-workers to obtain a one-pot multicomponent synthesis of benzopyrano-pyrrolidines 107 and pyrrole products 108 (Scheme 37). The latter cycloadducts were obtained when o-propargylic benzaldehydes were utihzed instead of o-allyhc benzalde-hydes, followed by in situ oxidation [72]. 

Likewise, an efficient one-pot multicomponent synthesis of annelated 2-amino pyridines (e.g., 17) utilizing [4+2] cycloadditions has been described <06JOC3494>. The process involves the in situ generation of 1-aza-1,3-butadiene from a palladium-catalyzed coupling-isomerization reaction of aryl halides (e.g., 18) with propargyl V-tosylamines (e.g., 19). The resulting butadiene then undergoes cycloadditions with V.S -ketene acetals (e.g., 20) to form annelated pyridines (e.g., 17). 

Bohn Rhoden CR, Westermann B, Wessjohann LA (2008) One-pot multicomponent synthesis of N-substituted tryptophan-derived diketopiperazines. Synthesis (Stuttg) 13 ... 

Rhoden CRB, Westermann B, Wessjoharm LA (2008) One-pot multicomponent synthesis of N-substituted tryptophan-derived diketopiperazines. Synthesis (Stuttg) (13) 2077-2082 Szardenings AK, Burkoth TS, Lu HH, Tien DW, Campbell DA (1997) A simple procedure for the solid phase synthesis of diketopiperazine and diketomorpholine derivatives. Tetrahedron 53(19) 6573-6593... 

This reaction was first reported by Robinson in 1917 and subsequently improved by Schopf in 1935. It is an ingenious one-pot multicomponent synthesis of tropinone from succindialdehyde, acetonedicarboxylic acid and methylamine in aqueous solution involving a double Mannich Reaction This reaction is thus known as the Robinson tropinone synthesis," Robinson synthesis, " Robinson-Schopf reaction,Robinson-Schopf condensation, or Robinson condensation." It has been reported that the Robinson tropinone synthesis can take place without any racemization at the stereogenic center adjacent to the aldehyde group, as demonstrated by the formation of L-a/to-teloidinone from D-tartaraldehyde, and c-a/to-teloidinone from i-tartaraldehyde respectively." ... 

Using this new sialyl phosphate donor 45, more than 50 different sialosides have been synthesized by combining several strategies (Fig. 7) that allow stereoselective, one-pot multicomponent synthesis of a-sialo oligosaccharides. These sialosides were further used in the preparation of a glycan array for the quantitative and... 

The use of hydrazines as a means to furnish the required N=N bond for pyridazine and its benzo derivatives was reported by several groups in 2013. Vlaar et al. developed a one-pot, multicomponent synthesis of 4-aminoph-thalazin-l(2fJ)-ones (APOs) 3 (Scheme 4) (13JOC6735). o-(Pseudo)halo-benzoates 4 were treated with hydrazines and isocyanide in the presence of palladium(II) acetate and Xantphos as bidentate phosphine ligand in dimethyl sulfoxide (DMSO) at 150°C, employing microwave irradiation conditions.These APOs were further functionalized via (a) an N2 alkylation... 

Spirooxindole derivatives are of considerable interest because of their broad biological properties. They are also structural motifs found in many classes of alkaloids and medicinal privileged compounds. In 2011, Macaev and coworkers demonstrated that (-)-(5)-brevicoUine (a p-carboline alkaloid) can be used, in a cycloaddition process, to catalyze one-pot multicomponent synthesis of spiro[oxoindole-3,4 -4 ... 

Y. Bai, J. Zeng, J. Ma, B. K. Gorityala, X.-W. Liu, J. Comb. Chem. 2010, 12, 696-699. Quick access to druglike heterocycles facile silver-catalyzed one-pot multicomponent synthesis of aminoindolizines. 

D. Castagnolo, L. Botta, M. Botta, Tetrahedron Lett. 2009, 50, 1526-1528. One pot multicomponent synthesis of 2,3-dihy-dropyrans new access to furanose-pyranose 1,3-C-C-linked-disaccharides. 

D. Bahulayan, V. S. Shinn, P. Pramitha, S. Arun, B. Sheeja, Synth. Commun. 2012,42, 1162—1176. Highly anfi -selective one-pot multicomponent synthesis of Mannich-type IV-acyl-ated P-amino acid derivatives hy copper or sodium salt catalysis. 

Imides forgotten players in the Ugi reaction. One-pot multicomponent synthesis of quinazolines. 

S. A. R. Mulla, T. A. Salama, M. Y. Pathan, S. M. Inamdar, S. S. Chavan, Tetrahedron Lett. 2013,54, 672-675. Solvent-free, highly efficient one-pot multicomponent synthesis of 1-amido- and 1-carbamato-alkyl naphthols/phenols catalyzed by ethylammonium nitrate as reusable ionic liquid under neat reaction condition at ambient temperature. 

R. S. Rao, K. Nagaiah, A. R. Prasad, Cat. Commun. 2006, 7, 797-801. Sulphamic acid an efficient, cost-effective and recyclable solid acid catalyst for three-component synthesis of homoaUyhc amines. Zirconyl chloride (ZiOClj) (d) B. Das, B. Ravikanth, K. R. Reddy, B. V. Rao, Helv. Chim. Acta 2007, 90, 105-109. Zirconyl chloride (=dichlorooxozir-conium) as an efficient catalyst for one-pot multicomponent synthesis of homoallylic amines. Sohd-supported perchloric acid (HClO -SiOj) (e) L. Nagarapu, V. Paparaju, G. Pathuri,... 

N. V. Lakshmi, P. Thirumurugan, K. Noorulla, P. Perumal, Bioorg. Med. Chem. Lett. 2010, 20, 5054—5061. InClj mediated one-pot multicomponent synthesis, anti-microbial, antioxidant and anticancer evaluation of 3-pyranyl indole derivatives. 

B. Das, K. Reddy, R. Ramu, P. Thirupathi, B. Ravikanth, Synlett 2006, 2006, 1756-1758. Iodine as an efficient catalyst for one-pot multicomponent synthesis of P-acetamido ketones. 

Maleki A (2013) One-pot multicomponent synthesis of diazepine derivatives using terminal alkynes in the presence of silica-supported superparamagnetic iron oxide nanoparticles. Tet Lett 54 2055-2059... 

Li-Yan Z, Chun C (2010) Iodine catalyzed one-pot multicomponent synthesis of a library of compounds containing tetrazolo[l,5-a]pyrimidine core. J Comb Chem 12 35-40... 

Keywords Aldehydes, dimedone, active methylene compounds, ammonium acetate, solvent-free, catalyst-free, room temperature, grinding, one-pot multicomponent synthesis, Hantzsch condensation, polyhydroquinolines... 

Keywords Hydrazine hydrate, ethyl acetoacetate, carbonyl compounds, malononitrile, ethanol, room temperature, Amberlyst A21, one-pot multicomponent synthesis, dihydropyrano [2,3-c]pyrazoles... 

Keywords Hydrazines, isatins, p-keto esters, malononitrile, ethyl cyanoacetate, piperidine, ethanol, room temperature, ultrasound irradiation, one-pot multicomponent synthesis, spiro[indoline-3,4 -pyrano[2,3-c]pyrazole] derivatives... 

A similar-type copper-catalyzed C-N coupling reaction for the one-pot multicomponent synthesis of substituted indulines was reported by Wang and his group. 

Keywords Isocyanides, carbodiimides, trimethylsUyl azide, methanol, room temperature, one-pot multicomponent synthesis, 1,5-disubstituted 1/7-tetrazoles... 

Keywords Acetphenones, aromatic aldehydes, thiols, BuOK, BuOH, room temperature, P-aryl-p-mercapto ketones, one-pot multicomponent synthesis, thio-Michael addition... 

Synthetic strategy One-pot multicomponent synthesis involving coupling-addition-cyclocondensation reactions... 

BiCla in situ generated from the procatalyst BiOCl was proved to be very efficient in the catalyzed one-pot multicomponent synthesis of P-acetamido ketones from a variety of aromatic aldehydes, enolizable ketones, acetyl chloride, and aceto or benzonitrile (Equation 13) [33cj. 

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