- Catalyst-free solventless synthesis of polysubstituted urea Method for preparing thioureas and chiral ureas and thiourea compounds
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The invention discloses a method for synthesizing polysubstituted urea, thiourea and chiral urea and thiourea compounds without catalyst without solvent, and the method comprises A contact reaction of an amine compound with a structure shown B as shown first in a non-catalyst and a solventless condition to prepare a polysubstituted urea or thiourea compound with a structure as shown C. R1 And R2 Each independently selected from a hydrocarbyl or substituted hydrocarbyl group, R3 The method is selected from H, hydrocarbyl or substituted hydrocarbyl, X is S or o. The method solves the defect that a catalyst and/or a solvent need to be used in the synthesis of urea and thiourea compounds in the prior art.
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Paragraph 0105-0111
(2021/09/29)
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- Hydroamination and Hydrophosphination of Isocyanates/Isothiocyanates under Catalyst-Free Conditions
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Symmetrical and unsymmetrical N,N’-disubstituted as well as trisubstituted ureas/thioureas by the hydroamination of isocyanates/isothiocyanates, and various phosphathioureas by the hydrophosphination of isothiocyanates have been synthesized in good to excellent yields under catalyst-free and mild conditions. This protocol is also applicable for the efficient synthesis of chiral ureas and thioureas and common herbicides, such as fenuron and monuron.
- Zhu, Xiancui,Xu, Mengchen,Sun, Jinrong,Guo, Dianjun,Zhang, Yiwei,Zhou, Shuangliu,Wang, Shaowu
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p. 5213 - 5218
(2021/10/19)
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- Tunable NIR-II emitting silver chalcogenide quantum dots using thio/selenourea precursors: Preparation of an MRI/NIR-II multimodal imaging agent
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Aqueous-stable, Cd- and Pb-free colloidal quantum dots with fluorescence properties in the second near-infrared region (NIR-II, 1000-1400) are highly desirable for non-invasive deep-tissue optical imaging and biosensing. The low band-gap semiconductor, silver chalcogenide, offers a non-toxic and stable alternative to existing Pd, As, Hg and Cd-based NIR-II colloidal quantum dots (QDs). We report facile access to NIR-II emission windows with Ag2X (X = S, Se) QDs using easy-to-prepare thio/selenourea precursors and their analogues. The aqueous phase transfer of these QDs with a high conservation of fluorescence quantum yield (retention up to ~90%) and colloidal stability is demonstrated. A bimodal NIR-II/MRI contrast agent with a tunable fluorescence and high T1 relaxivity of 408 mM-1 s-1 per QD (size ~ 2.2 nm) and 990 mM-1 s-1 per QD (size ~ 4.2 nm) has been prepared by grafting 50 and 120 monoaqua Gd(iii) complexes respectively to two differently sized Ag2S QDs. The size of the nanocrystals is crucial for tuning the Gd payload and the relaxivity.
- Basel, Siddhant,Bhardwaj, Karishma,Borthakur, Sukanya,Brito, Beatriz,Clarke, Mitchell,Pariyar, Anand,Pradhan, Sajan,Roy, Pankaj,Saikia, Lakshi,Shankar, Amit,Stasiuk, Graeme J.,Tamang, Sudarsan,Thapa, Surakcha
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supporting information
p. 15425 - 15432
(2020/11/18)
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- Hydrogen-Bond Catalysis of Imine Exchange in Dynamic Covalent Systems
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The reversibility of imine bonds has been exploited to great effect in the field of dynamic covalent chemistry, with applications such as preparation of functional systems, dynamic materials, molecular machines, and covalent organic frameworks. However, acid catalysis is commonly needed for efficient equilibration of imine mixtures. Herein, it is demonstrated that hydrogen bond donors such as thioureas and squaramides can catalyze the equilibration of dynamic imine systems under unprecedentedly mild conditions. Catalysis occurs in a range of solvents and in the presence of many sensitive additives, showing moderate to good rate accelerations for both imine metathesis and transimination with amines, hydrazines, and hydroxylamines. Furthermore, the catalyst proved simple to immobilize, introducing both reusability and extended control of the equilibration process.
- Schaufelberger, Fredrik,Seigel, Karolina,Ramstr?m, Olof
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supporting information
p. 15581 - 15588
(2020/10/02)
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- Unclicking of thioureas: Base catalyzed elimination of anilines and isothiocyanates from thioureas
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Bisaromatic thioureas are widely used in e.g. asymmetric organocatalysis and considered to be robust compounds. Herein we show, in strong contrast to common notion, that thioureas dissociate to amines and isothiocyanates in a base catalyzed reaction under mild conditions. This ‘unclicking’ process can occur in the presence of weak organic bases even at moderate temperatures. The influence of the substituents at the aromatic rings of the thiourea on the regioselectivity of this unclicking process is also shown.
- Vlatkovi?, Matea,Feringa, Ben L.
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p. 2188 - 2192
(2019/03/05)
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- Micelle-Enabled One-Pot Guanidine Synthesis in Water Directly from Isothiocyanate using Hypervalent Iodine(III) Reagents under Mild Conditions
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In this work, we developed a one-pot synthesis of guanidine directly from isothiocyanate using DIB (diacetoxyiodobenzene) as a desulfurizing agent under micellar conditions in water. Our optimization study revealed that the use of 1 % TPGS-750-M as a surfactant with NaOH as an additive base at room temperature can convert a variety of isothiocyanates and amines into corresponding guanidines in excellent yields (69–95 %). This synthetic process in water can be applied to prepare guanidine at gram-scale quantity. Our aqueous micellar medium also demonstrated high reusability as the reaction can be performed for several cycles without losing its efficiency. The reaction is metal-free, utilizes water as solvent and practical (room temperature and open flask).
- Srisa, Jakkrit,Tankam, Theeranon,Sukwattanasinitt, Mongkol,Wacharasindhu, Sumrit
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p. 3335 - 3343
(2019/09/12)
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- Nickle Catalysis Enables Access to Thiazolidines from Thioureas via Oxidative Double Isocyanide Insertion Reactions
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An efficient synthesis of thiazolidine-2,4,5-triimine derivatives was developed via Ni-catalyzed oxidative double isocyanide insertion to thioureas under air conditions, in which thioureas play three roles as a substrate, a ligand, and overcoming isocyanide polymerization. The reaction is featured by employing a low-cost and low loading Ni(acac)2 catalyst, without any additives, and high atom economy. This is the first example to directly apply a Ni(II) catalyst in oxidative double isocyanide insertion reactions.
- Yuan, Wen-Kui,Liu, Yan Fang,Lan, Zhenggang,Wen, Li-Rong,Li, Ming
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supporting information
p. 7158 - 7162
(2018/11/25)
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- 2-Picolylamino(diphenylphosphinoselenoic)amide supported zinc complexes: Efficient catalyst for insertion of N–H bond into carbodiimides, isocyanates, and isothiocyanate
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We report here the hydroamination of heterocumulenes such as carbodiimides, isocyanates, and isothiocyanates by zinc complexes supported by the ligand 2-picolylamino-(diphenylphosphinoselenoic)amide [{(Ph2P-(?Se)}2NCH2(C5H4N)] (1). A series of zinc complexes [κ2-{(Ph2P-(?Se)}2NCH2(C5H4N)ZnX2] [(X?Cl (2), Br (3a), I (4)] were prepared from ligand 1 and the corresponding zinc dihalide in a 1:1 molar ratio at 60°C in a chloroform solvent. The reaction of ligand 1 and ZnBr2 in methanol yielded another zinc complex [κ2-{(Ph2P-(?Se)}2NCH2(C5H4N)ZnBr2(CH3OH)] (3b). The molecular structures of compounds 3a, 3b, and 4 were established through single-crystal X-ray diffraction analyses. The solid-state structures of all the complexes revealed a κ2- chelation through pyridine nitrogen and selenium atoms of ligand 1 to the zinc ion. Complex 2 proved to be a competent pre-catalyst for the addition of the amine N–H bond to carbodiimides, isocyanates, and isothiocyanates. The reaction scope was expanded to reactions of aliphatic and aromatic amines with phenylisocyanate and phenylisothiocyanate in toluene solvents, which proceeded rapidly at room temperature with 5 mol% catalyst loading to yield (up to 99%) the corresponding derivatives of urea and thio-urea. However, a temperature of 90°C was needed for the hydroamination of N,N′ dicyclohexylcarbodiimide. We also report the most plausible mechanism of the hydroamination reaction.
- Harinath, Adimulam,Bano, Kulsum,Ahmed, Shakil,Panda, Tarun K.
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supporting information
p. 23 - 32
(2017/09/25)
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- PROCESS FOR THE PRODUCTION OF 5-HYDROXYMETHYLFURFURAL IN THE PRESENCE OF ORGANIC CATALYSTS FROM THE THIOUREA FAMILY
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A process for the transformation of a feed of at least one sugar into 5-hydroxymethylfurfural, contacting the feed with one or more organic catalysts in the presence of at least one solvent, said solvent being water or an organic solvent, alone or as a mi
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Paragraph 0057-0059
(2019/01/10)
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- A facile method for the preparation of carbodiimides from thioureas and (Boc)2O
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A concise method for the preparation of carbodiimides from thioureas using di-tert-butyl dicarbonate [(Boc)2O] as the dehydrosulfurizative reagent has been developed. Using DMAP as the catalyst, a variety of symmetric and asymmetric 1,3-diaryl thioureas were converted into the corresponding carbodiimides efficiently in a short time.
- Wu, He,Sun, Yan-Fang,Zhang, Chen,Miao, Chun-Bao,Yang, Hai-Tao
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supporting information
p. 739 - 742
(2018/01/27)
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- Thiocarbonyl Surrogate via Combination of Sulfur and Chloroform for Thiocarbamide and Oxazolidinethione Construction
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An efficient and practical thiocarbonyl surrogate via combination of sulfur and chloroform has been developed. A variety of thiocarbamides and oxazolidinethiones have been established, including chiral thiourea catalysts and chiral oxazolidinethione auxiliaries with high selectivity. Meanwhile, pesticides Diafenthiuron (an acaricide), ANTU (a rodenticide), and Chloromethiuron (an insecticide) were practically synthesized through this method in gram scale. Dicholorocarbene, as the key intermediate, was further confirmed via a carbene-trapping control experiment.
- Tan, Wei,Wei, Jianpeng,Jiang, Xuefeng
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supporting information
p. 2166 - 2169
(2017/04/27)
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- An isocyanide based multi-component reaction under catalyst- and solvent-free conditions for the synthesis of unsymmetrical thioureas
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A new and efficient method for the synthesis of thiourea derivatives by a sequential one-pot, three-component reaction between aromatic isocyanides, amines, and 1,2-di-tert-butyldisulfane (DTBS) was developed and 27 different examples were synthesized in good to excellent yields. DTBS was identified as an effective sulfur surrogate without the use of both catalysts and solvents. This protocol does not employ any transition metal catalyst or special experimental setup.
- Singh, Karandeep,Sharma, Siddharth
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p. 197 - 201
(2016/12/28)
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- Dual roles of substituted thiourea as reductant and ligand in CuAAC reaction
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A highly efficient catalytic system, CuSO4·5H2O/1-(4-methoxyphenyl)-3-phenylthiourea, for the copper(I)-catalyzed azide–alkyne cycloaddition reaction (CuAAC) was discovered. In the above catalytic system, substituted thiourea acts both as a reductant and a ligand. CuSO4·5H2O/1-(4-methoxyphenyl)-3-phenylthiourea is both an economical and efficient catalyst for the CuAAC reaction. In addition, the new catalytic system has advantageous features including mild and green reaction conditions, and broad substrate compatibility. A variety of 1,4-disubstituted 1,2,3-triazoles have been prepared with good to excellent yields with the CuSO4·5H2O/1-(4-methoxyphenyl)-3-phenylthiourea catalytic system in aqueous solution.
- Wang, Siyu,Jia, Kai,Cheng, Jiajia,Chen, Yu,Yuan, Yaofeng
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supporting information
p. 3717 - 3721
(2017/09/01)
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- Molecular modeling and synthesis of some new 2-imino-4-thiazolidinone derivatives with promising TNF-α inhibitory activity
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A new series of thirty two 2-imino-4-thiazolidinone derivatives were synthesized, and the synthesized compounds were docked for in silico studies against the TNF-α target. The predicted results were confirmed through an in vitro TNF-α study which revealed that compounds 3f and 3g showed better TNF-α inhibition as compared to the standard drug indomethacin without causing any cytotoxicity. Fourteen compounds exhibiting significant in vitro TNF-α activity were further tested for in vivo anti-inflammatory activity by a carrageenan induced method. Compounds 3f and 3g showed better inhibition of inflammation in vivo as compared to the standard drug without causing any damage to the stomach. Furthermore, an immunohistochemical study showed that the compounds 3f and 3g exhibited better reduction in protein expression of TNF-α as compared to indomethacin. The in silico, in vitro and in vivo studies suggested that the compounds 3f and 3g might be considered as potent anti-inflammatory agents.
- Ali, Yakub,Alam, Mohammad Sarwar,Hamid, Hinna,Husain, Asif,Dhulap, Abhijeet,Hussain, Firasat,Bano, Sameena,Kharbanda, Chetna
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p. 711 - 723
(2016/01/12)
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- Convenient synthesis of unsymmetrical N,N′-disubstituted thioureas in water
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A simple and convenient two-step method has been developed and used to synthesise 25 (4 of which are novel) unsymmetrical N,N′-disubstituted thioureas in water. Alkylamines or variously substituted arylamines reacted smoothly with phenyl chlorothionoformate at room temperature to form thiocarbamates, which were then reacted with another alkyl- or arylamine in water at reflux to afford the unsymmetrical N,N′-disubstituted thioureas in good to excellent yields. Mild conditions, simple work-up, high yields as well as using water as solvent are the major advantages of the method.
- Li, Zhengyi,Chen, Yuan,Yin, Yue,Wang, Zhiming,Sun, Xiaoqiang
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p. 670 - 673
(2016/11/18)
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- Synthesis of some 3,5-disubstituted phenyl-5,6-dihydrofuro[2,3-d]thiazol-2(3H)-ylidene) imines as potential pesticides
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A new series of novel 3,5-disubstituted phenyl-5,6-dihydrofuro[2,3-d]thiazol-2(3H)-ylidene) imines have been synthesized from a common intermediate, in good yield. These compounds have been screened for their herbicidal activities against èchinochloa oryzicola, Echinochloa crus-galli, Oryza sativa, Glycine max and antifungal activities against Aspergillus Niger and Pyricularia oryzae whereas for antimicrobial activities, they have been screened against Salmonella typhi, Escherichia coli, Klebsiella pneumoniae, Bacillus subtilis and Bacillus pumilus.
- Tiwari, Shailendra,Singh, Kamal Pratap,Ahmad, Akeel
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p. 1007 - 1012
(2017/11/10)
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- Synthesis of phosphaguanidines by hydrophosphination of carbodiimides with phosphine boranes
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The direct addition of anionic secondary phosphine boranes to carbodiimides yields both chiral and achiral phosphaguanidine boranes under ambient temperature conditions. An analogous preparation of menthol-derived phosphinite boranes is also described. These products can be deborinated to give the corresponding phosphines, and subsequently oxidized to give phosphine oxides. The robustness of this method was further demonstrated in the synthesis of structurally novel cyclic phosphaguanidines. (Chemical Equation Presented).
- Busacca, Carl A.,Milligan, John A.,Rattanangkool, Eakkaphon,Ramavarapu, Cyrus,Chen, Anji,Saha, Anjan K.,Li, Zhibin,Lee, Heewon,Geib, Steven J.,Wang, Guijun,Senanayake, Chris H.,Wipf, Peter
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p. 9878 - 9887
(2015/01/09)
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- A model for a solvent-free synthetic organic research laboratory: Click-mechanosynthesis and structural characterization of thioureas without bulk solvents
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The mechanochemical click coupling of isothiocyanates and amines has been used as a model reaction to demonstrate that the concept of a solvent-free research laboratory, which eliminates the use of bulk solvents for either chemical synthesis or structural characterization, is applicable to the synthesis of small organic molecules. Whereas the click coupling is achieved in high yields by simple manual grinding of reactants, the use of an electrical, digitally controllable laboratory mill provides a rapid, quantitative and general route to symmetrical and non-symmetrical aromatic or aromatic-aliphatic thioureas. The enhanced efficiency of electrical ball milling techniques, neat grinding or liquid-assisted grinding, over manual mortar-and-pestle synthesis is demonstrated in the synthesis of 49 different thiourea derivatives. Comparison of powder X-ray diffraction data of mechanochemical products with structural information found in the Cambridge Structural Database (CSD), or obtained herein through single crystal X-ray diffraction, indicates that the mechanochemically obtained thiourea derivatives are pure in a chemical sense, but can also demonstrate purity in a supramolecular sense, i.e. in all structurally explored cases the product consisted of a single polymorph. As an extension of our previous work on solvent-free synthesis of coordination polymers, it is now demonstrated that such polymorphic and chemical purity of selected thiourea derivatives, the latter being evidenced through quantitative reaction yields, can enable the direct solvent-free structural characterization of mechanochemical products through powder X-ray diffraction aided by solid-state NMR spectroscopy.
- Strukil, Vjekoslav,Igrc, Marina D.,Fabian, Laszlo,Eckert-Maksic, Mirjana,Childs, Scott L.,Reid, David G.,Duer, Melinda J.,Halasz, Ivan,Mottillo, Cristina,Friscic, Tomislav
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supporting information
p. 2462 - 2473
(2013/02/21)
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- Structural requirement of phenylthiourea analogs for their inhibitory activity of melanogenesis and tyrosinase
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Effect of a series of 1-phenylthioureas 1a-k and 1,3-disubstituted thioureas 2a-k were evaluated against melanin formation in melanoma B16 cell line and mushroom tyrosinase. Inhibitory activity of tyrosinase of 1-phenylthioureas 1a-k is parallel to their melanogenic inhibition. Thus, the melanogenic inhibition in melanoma B16 cells of 1-phenylthioureas could be the result of inhibition of tyrosinase. However, 1,3-diaryl or 1-phenyl-3- alkylthioureas, 2a-k, appears as melanogenic inhibitor without inhibition of tyrosinase. The molecular docking study of 1e and 2b to binding pocket of tyrosinase provided convincing explanation regarding the necessity of direct connection of planar phenyl to thiourea unit without N′-substitution of phenylthioureas 1 as tyrosinase inhibitor and 2 as non-tyrosinase inhibitor.
- Thanigaimalai, Pillaiyar,Lee, Ki-Cheul,Sharma, Vinay K.,Joo, Cheonik,Cho, Won-Jea,Roh, Eunmiri,Kim, Youngsoo,Jung, Sang-Hun
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experimental part
p. 6824 - 6828
(2011/12/22)
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- Highly efficient and catalyst-free synthesis of unsymmetrical thioureas under solvent-free conditions
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A highly efficient and simple synthesis of unsymmetrical thioureas is reported based on the reaction of readily synthesized dithiocarbamates with amines, without using any catalyst under solvent-free conditions. The short reaction time, high yields, and s
- Halimehjani, Azim Ziyaei,Pourshojaei, Yaghoub,Saidi, Mohammad R.
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scheme or table
p. 32 - 34
(2009/04/10)
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- 5-SUBSTITUTED-2-IMINO-THIAZOLIDINONE COMPOUNDS AND THEIR USE AS INHIBITORS OF BACTERIAL INFECTION
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A method for inhibiting Gram-negative bacterial pathogenesis, a method of screening for compounds that inhibit type III secretion in Gram-negative bacteria, and compounds that inhibit type III secretion in Gram-negative bacteria.
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Page/Page column 44
(2010/01/29)
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- Synthesis, phytotoxic, cytotoxic, acetylcholinesterase and butrylcholinesterase activities of N,N-diaryl unsymmetrically substituted thioureas
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Fourteen N,N-diaryl unsymmetrically substituted thioureas were synthesised and their cytotoxic (in vitro), phytotoxic (in vitro), acetylcholinesterase and butrylcholinesterase activities were determined. Thiourea 16 exhibited high, and 1 and 3 showed significant phytotoxic activity. Thioureas 1, 3, 4, 6 and 10 showed significant activity and 2, 6 and 7 indicated moderate cytotoxic activities. Compound 12 exhibited butrylcholinesterase activity higher than a standard reference.
- Begum, Saeedan,Choudhary, M. Iqbal,Khan, Khalid M.
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experimental part
p. 1719 - 1730
(2010/05/18)
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- Substituted 2-Imino-5-arylidenethiazolidin-4-one Inhibitors of Bacterial Type III Secretion
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Diverse species of pathogenic Gram-negative bacteria use secretion systems to export a variety of protein toxins and virulence factors that help establish and maintain infection. Disruption of such secretion systems is a potentially effective therapeutic strategy. We developed a high-throughput screen and identified a trisaryl substituted 2-imino-5-arylidenethiazolidin-4-one, compound 1, as an inhibitor of the type III secretion system. Expansion of this chemotype enabled us to define the essential pharmacophore for type III secretion inhibition by this structural class. A synthetic diversity set helped us identify N-3 as the most permissive locus and led to the design of a panel of novel N-3-dipeptide-modified congeners with improved activity and physiochemical properties. We now report on the synthesis of these compounds, including a novel solid phase approach to the rapid generation of the dipeptide-thiazolidinone hybrids, and their in vitro characterization as inhibitors of type III secretion in Salmonella enterica serovar Typhimurium.
- Kline, Toni,Felise, Heather B.,Barry, Kathleen C.,Jackson, Stona R.,Nguyen, Hai V.,Miller, Samuel I.
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supporting information; experimental part
p. 7065 - 7074
(2009/11/30)
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- Antimicrobial activity and structural study of disubstituted Thiourea Derivatives
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The antimicrobial activity of six N-phenyl- and fourteen N-benzoylthiourea derivatives were evaluated from their Minimal Inhibitory Concentration (MIC) values using the microdilution procedure against ten microorganisms. Most of the compounds exhibited selective activity against fungi and Gram-positive bacteria, which were very effectively inhibited by some of the tested thioureas. Additionally, SAR considerations and four novel X-ray diffraction structures of N-benzoylthioureas are included. Springer-Verlag 2007.
- Cunha, Silvio,MacEdo Jr., Fernando C.,Costa, Giselle A. N.,Rodrigues Jr., Manoel T.,Verde, Rosival B. V.,De Souza Neta, Lourdes C.,Vencato, Ivo,Lariucci, Carlito,Sa, Fernando P.
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p. 511 - 516
(2008/02/03)
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- Kinetics of condensation of aryl isothiocyanates with aryl amines
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The kinetics of condensation of aryl isothiocyanates with aryl amines in non-aqueous medium have been investigated. The condensation reaction is first order each in [amines] and [isothiocynates]. The effect of substituents on the rate of condensation and the thermodynamic parameters are evaluated. The reaction products have been isolated and characterized as asymmetric thiocarbamides and a probable mechanism of the condensation proposed.
- Pathrikar, Late G. Y.,Bondge,Burungale,Bhingolikar,Ingle,Mane
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p. 2518 - 2521
(2007/10/03)
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- 1-(Methyldithiocarbonyl)imidazole: A useful thiocarbonyl transfer reagent for synthesis of substituted thioureas
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1-(Methyldithiocarbonyl)imidazole 1 and its N-methyl quaternary salt 2 have been shown to be efficient methyldithiocarbonyl and thiocarbonyl transfer reagents for the synthesis of dithiocarbamates, symmetrical and unsymmetrical mono-, di- and tri-substituted thioureas in high yields under mild and simple non-hazardous reaction conditions. (C) 2000 Elsevier Science Ltd.
- Mohanta, Pramod K.,Dhar, Sanchita,Samal,Ila,Junjappa
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p. 629 - 637
(2007/10/03)
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- Unsymmetrically N,N′-Disubstituted Diarylthioureas and Their Coordination Compounds with Cu(II) and Ni(II)
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Some new unsymmetrically N,N′-disubstituted diarylthioureas were prepared, and their reactions of complex formation in solutions were studied. Coordination compounds of the synthesized thioureas with 3d metals(2+) (Cu, Ni) were isolated and shown to have a chelate structure of the general formula M(SN)2.
- Cheresova,Zhukova,Tatarintseva,Cheresov,Mukmeneva
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p. 1271 - 1275
(2007/10/03)
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- Influence of Substituents on the Synthesis of Thiazolidinones
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The influence of substituents (subunits) in the synthesis of thiazolidinones by the reaction of unsymmetrical thioureas with monochloroacetic acid in ethanol has been rationalised by the characterisation of the hydrolysis products of the resulting thiazolidinones.The formation of thiol from thiourea, which is the key intermediate in thiazolidinone synthesis, invariably involves the -NH- group adjacent to more electron withdrawing subunits.
- Sabu, M.,Garnaik, B. K.,Behera, Rajani K.
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p. 779 - 781
(2007/10/02)
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- Derivatives of Imidazolidines from Oxalic Amidines
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Tetraarylsubstituted oxalic amidines 1 react with acyl chlorides, phosgene, thiophosgene, chlorocarbonylsulfenylchloride, isocyaniddichlorides, and N-aroyl-1-chlorothio-formimidoylchlorides 7 to give the corresponding 5-membered heterocycles 3,4,5 and 8.Isocyanates 9 and isothiocyanates 10 react with oxalic amidines to yield imidazolidines 11, 12 and ureas 13, 14.Hydrolysis of 3-5, 8, 11, 12 leads to the corresponding oxo compounds 15, 16.
- Beckert, R.,Mayer, R.
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p. 227 - 236
(2007/10/02)
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