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1.
A convenient synthis for 4‐substituted and 3,4‐disubstituted 1,7‐naphthyridine‐2(1H)‐thiones 7 has been developed. The method is based on the electrocyclic reaction of 4‐(1‐arylalk‐1‐enyl)‐3‐isothiocyanatopyridines 6 , generated in situ by the treatment of the respective isocyanides 5 with S8 in the presence of a catalytic amount of selenium. The isocyanides 5 can be easily prepared from commercially available pyridin‐3‐amine by conventional organic reactions. 相似文献
2.
Reaction of substituted o‐aminobenzyl chlorides with isocyanides in the presence of a weak base (NaHCO3) at room temperature afforded the diversely functionalized 2‐aminoindoles in good to excellent yields. A formal [4+1] cycloaddition of the in situ generated aza‐ortho‐xylylenes with isocyanides accounted for the reaction outcome. 相似文献
3.
Issa Yavari Jamil Sheykhahmadi Hamed Saffarian Nooshin Zahedi Samira Bahemmat Mohammad Reza Halvagar 《合成通讯》2013,43(19):2608-2614
AbstractThe four-component reaction among arylhydrazine, alkyl acetoacetate derivatives, alkyl isocyanides, and dialkyl acetylenedicarboxylates, leading to the formation of dialkyl 2-[(Z)-(alkylamino)(3-alkyl-5-oxo-1-phenyl-1,5-dihydro-4H-pyrazol-4-ylidene)methyl] fumarates is described. The structure of target compounds was confirmed using X-ray diffraction study. These pyrazolone derivatives contain a highly twisted exocyclic 1,3-butadiene moiety with skew (??=?87°) geometry. 相似文献
4.
Mehdi Adib MohammadHosein Sayahi Niusha Mahmoodi HamidReza Bijanzadeh 《Helvetica chimica acta》2006,89(6):1176-1180
The reactive 1 : 1 zwitterionic intermediate formed by the addition of isocyanides to dialkyl acetylenedicarboxylates was trapped with 4‐arylurazoles to produce the highly functionalized pyrazolo[1,2‐a][1,2,4]triazoles 5 in good yields (Table). The structures of the products 5a – h were corroborated spectroscopically (IR, 1H‐ and 13C‐NMR), by EI‐MS, and elemental analysis. A possible mechanism for this reaction is proposed (Scheme). 相似文献
5.
Efficient Solvent‐Free Synthesis of Benzothiazine‐Fused Pyrrolo[3,4‐c]coumarins: Cycloaddition Reactions between Coumarin‐Based Dihydrobenzothiazoles and Isocyanides
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Mehdi Khoobi Ali Ramazani Mohammad Mahdavi Alireza Foroumadi Saeed Emami Sang Woo Joo Katarzyna Ślepokura Tadeusz Lis Abbas Shafiee 《Helvetica chimica acta》2014,97(6):847-853
A new and unusual synthesis of benzothiazine‐fused pyrrolo[3,4‐c]coumarins, involving the ring‐opening of coumarin‐based dihydrobenzothiazoles and subsequent [4+1] cycloaddition reaction with isocyanides, was described. Thus, simple heating of various 3‐(2,3‐dihydro‐2‐methylbenzo[d]thiazol‐2‐yl)coumarins with isocyanides produced the title compounds in good yields under solvent‐free conditions. 相似文献
6.
De Novo Synthesis of Imidazoles by Visible‐Light‐Induced Photocatalytic Aerobic Oxidation/[3+2] Cycloaddition/Aromatization Cascade
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Qiao‐Hui Deng You‐Quan Zou Dr. Liang‐Qiu Lu Prof. Dr. Zi‐Long Tang Dr. Jia‐Rong Chen Prof. Dr. Wen‐Jing Xiao 《化学:亚洲杂志》2014,9(9):2432-2435
A visible‐light‐induced photocatalytic aerobic oxidation/[3+2] cycloaddition/aromatization cascade between secondary amines and isocyanides has been successfully developed. The reaction provides a general and efficient access to diversely substituted imidazoles and imidazo[1,5‐a]quinoxalin‐4(5 H)‐ones in good yields under mild conditions. 相似文献
7.
Formation of Phosphorylated 3H‐Pyrroles from NefIsocyanidePerkow Adducts and Tosylmethyl Isocyanide
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Imidoyl chlorides, generated from isocyanides and acyl chlorides, react with trialkyl phosphites, in a Perkow‐type reaction, to afford 3‐(alkylimino)‐2‐[(dialkyloxyphosphoryl)oxy]acrylates, which undergo a smooth reaction with tosylmethyl isocyanide (TsMIC) to furnish 4‐(alkylamino)‐3‐[(dialkyloxyphosphoryl)oxy]‐5‐[(4‐methylphenyl)sulfonyl]‐3H‐pyrrole‐3‐carboxylates in moderate‐to‐good yields. 相似文献
8.
Azizollah Habibi Leyla Mousavifar Issa Yavari Mohammad R. Yazdanbakhsh 《Monatshefte für Chemie / Chemical Monthly》2007,4(8):603-606
Alkyl isocyanides undergo a smooth reaction with alkylidene Meldrum’s acids in the presence of arylhydroxylamines to produce N
1-alkyl-2-(3,5-dioxo-2-aryltetrahydro-4-isoxazolyl)alkanamides in high yields. 相似文献
9.
Azizollah Habibi Leyla Mousavifar Issa Yavari Mohammad R. Yazdanbakhsh 《Monatshefte für Chemie / Chemical Monthly》2007,138(6):603-606
Summary. Alkyl isocyanides undergo a smooth reaction with alkylidene Meldrum’s acids in the presence of arylhydroxylamines to produce N
1-alkyl-2-(3,5-dioxo-2-aryltetrahydro-4-isoxazolyl)alkanamides in high yields. 相似文献
10.
[Ph3C][B(C6F5)4]: A Highly Efficient Metal‐Free Single‐Component Initiator for the Helical‐Sense‐Selective Cationic Copolymerization of Chiral Aryl Isocyanides and Achiral Aryl Isocyanides
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Dr. Xinwen Yan Prof. Shaowen Zhang Dr. Pengfei Zhang Dr. Xiaolu Wu An Liu Ge Guo Prof. Yuping Dong Prof. Xiaofang Li 《Angewandte Chemie (International ed. in English)》2018,57(29):8947-8952
Commercially available [Ph3C][B(C6F5)4] served as a highly efficient metal‐free and single‐component initiator not only for the carbocationic polymerization of polar and bulky aryl isocyanides with extremely high activity up to 1.2×107 g of polymer/(molcat. h), but also for the helical‐sense‐selective polymerization of chiral aryl isocyanides and copolymerization with achiral aryl isocyanides to afford high‐molecular‐weight functional poly(aryl isocyanide)s with good solubility as well as AIE characteristics and/or a single‐handed helical conformation. 相似文献
11.
Lothar Weber 《Angewandte Chemie (International ed. in English)》1998,37(11):1515-1517
Novelties and surprises in the chemistry of metal isocyanides : The synthesis and structure determination of homoleptic isocyanide metalates [M(CNXyl)m]− (M=Co, m=4; M=Mn, m=5; Xyl=2,6-Me2C6H3) indicate that we need to revise our understanding of transition metal–isocyanide interactions. Further investigations will be required to determine whether these salts with isocyanide metalate ions display a chemistry as rich as that of the analogous carbonyl metalates. 相似文献
12.
Zahra Tanbakouchian Mohammad Ali Zolfigol Behrouz Notash Maryam Ranjbar Morteza Shiri 《应用有机金属化学》2019,33(8)
Four distinct sets of functionalized quinolines were synthesized by reacting 2‐chloroquinoline‐3‐carbonitriles with various types of isocyanides under appropriate conditions. The palladium‐catalysed reaction of less hindered aliphatic and aromatic isocyanides with 2‐chloroquinoline‐3‐carbonitriles yielded 2‐alkyl(aryl)‐1‐imino‐1H‐pyrrolo[3,4‐b]quinolin‐3(2H)‐one derivatives; however, the catalysed reaction of more hindered isocyanides such as tert‐butyl isocyanide produced the corresponding 3‐cyanoquinoline‐2‐carboxamides. Interestingly, chloroquinoline‐3‐carbonitriles reacted with ethyl isocyanoacetate in the presence of Cs2CO3 to generate imidazo[1,5‐a]quinoline derivatives; notably, tosylmethyl isocyanide under the same conditions formed unprecedented 2‐tosyl‐3‐cyanoquinolines. 相似文献
13.
Saeed Balalaie Mohammad Ali Bigdeli Enayatollah Sheikhhosseini Azizollah Habibi Hamed Piri Moghadam Mehrnoush Naderi 《Helvetica chimica acta》2012,95(3):528-535
The novel coumarin‐3‐carboxamides (=2‐oxo‐2H‐1‐benzopyran‐3‐carboxamides) 5a – 5g containing lipophilic spacers were synthesized through the Ugi‐four‐component reaction (Scheme 1). The reactions of aromatic aldehydes 1 , 4,4′‐oxybis[benzenamine] or 4,4′‐methylenebis[benzenamine] as diamine 2 , coumarin‐3‐carboxylic acid (=2‐oxo‐2H‐benzopyran‐3‐carboxylic acid; 3 ), and alkyl isocyanides 4 lead to the desired substituted coumarin‐3‐carboxamides 5a – 5g at room temperature with high bond‐forming efficiency. These novel coumarin derivatives exhibit brilliant fluorescence at 544 nm in CHCl3. 相似文献
14.
A variety of simple alkyl and aryl isocyanides have been polymerized using 0.5% NiCl2 in ethanol as a catalyst. The resulting poly(iminomethylenes) have been characterized by carbon-13 NMR spectroscopy and their polystyrene-equivalent molecular weights have been determined by gel permeation chromatography. Straight chain aliphatic isocyanides having from three to ten carbon atoms in the chain form readily solyble polymers having molecular weights (Mw) in the general range 10,000 to 30,000. Neopentyl isocyanide unlike tert-butyl isocyanide forms an insoluble polymer. A number of new soluble aryl isocyanide polymers have been obtained. However, aryl isocyanides having a single alkyl substituent (CH3, C2H5, CF3) in the ortho position give only insoluble polymers, whereas aryl isocyanides having alkyl substituents in both ortho positions (e.g., 2,6-(CH3)2C6H3NC and 2,4,6-(CH3)3C6H2NC) fail to polymerize under these conditions. The highest molecular weight soluble aryl isocyanide homopolymer is obtained from 3-CH3OC6H4NC(Mw = 26,000). The trimethylsilyl substituted isocyanide (CH3)3SiCH2CH2NC has been obtained from LiCH2NC and (CH3)SiCH2Cl and gives a brown soluble homopolymer with a molecular weight (Mw) of 19,000. 相似文献
15.
The HRP mass spectra of some alkyl isocyanides (R? NC in which R equals CH3, C2H5, n-C3H7, n-C4H9 and t-C4H9) and two methyl branched alkyl cyanides (R? CN in which R equals i-C3H7 and t-C4H9) have been studied. Using metastable ion transitions and appearance potentials, the fragmentation patterns and spectral characteristics of the isocyanides can be given. A comparison has been made with the mass spectral data of the corresponding cyanides. Although the mass spectra of alkyl cyanides and isocyanides show close relationship, evidence could be obtained that this resemblance is not caused by rearrangement of the isocyanide into cyanide molecules. The main difference between the spectra of both compounds is caused by the strength of the α-bond, being weaker in the case of the isocyanides. The abundance of ions formed by α-bond cleavage decreases with increasing size of the alkyl group. 相似文献
16.
《Angewandte Chemie (Weinheim an der Bergstrasse, Germany)》2017,129(15):4374-4377
Isocyanides are exceptional building blocks, the wide deployment of which in multicomponent and metal‐insertion reactions belies their limited availability. The first conjugate addition/alkylation to alkenyl isocyanides is described, which addresses this deficiency. An array of organolithiums, magnesiates, enolates, and metalated nitriles add conjugately to β‐ and β,β‐disubstituted arylsulfonyl alkenyl isocyanides to rapidly assemble diverse isocyanide scaffolds. The intermediate metalated isocyanides are efficiently trapped with electrophiles to generate substituted isocyanides incorporating contiguous tri‐ and tetra‐substituted centers. The substituted isocyanides are ideally functionalized for elaboration into synthetic targets as illustrated by the three‐step synthesis of γ‐carboline N ‐methyl ingenine B. 相似文献
17.
R. B. King L. Borodinsky M. J. Greene 《Journal of polymer science. Part A, Polymer chemistry》1987,25(8):2165-2173
Copolymerization of an isocyanide giving an insoluble homopolymer with another isocyanide giving a soluble homopolymer in ethanol solution using 0.5–1% of a nickel (II) catalyst in many cases gives a soluble copolymer containing pendant groups arising from both isocyanides. Thus, methyl isocyanide, which gives an insoluble homopolymer, gives chloroform-soluble copolymers incorporating 39–44% of pendant methyl groups when copolymerized with equimolar amounts of tert-butyl isocyanide or several aryl isocyanides. Similarly, cyclohexyl isocyanide, which also gives an insoluble homopolymer, gives chloroform-soluble copolymers incorporating 43–59% of pendant cyclohexyl groups when copolymerized with equimolar amounts of several aryl isocyanides. The compositions, chloroform solubilities, and polystyrene equivalent molecular weights are given for 33 different copolymers obtained by copolymerizations of various equimolar binary mixtures of the monomers CH3NC, (CH3)3CNC, cyclo-C6H11NC, C2H5NC, CH3CH?CHNC,(CH3)2C?CHNC, 2,4,6-(CH3)3C6H2CH?CHNC, C6H5CH(CH3)NC, CH2?CHNC, (CH3)3CCH?CHNC, C6H5NC, 2- and 4-CH3C6H4NC and 2-, 3-, 4-CH3OC6H4NC using the nickel (II) catalyst system. 相似文献
18.
Issa Yavari Mohammad Anary-Abbasinejad Abdolali Alizadeh 《Monatshefte für Chemie / Chemical Monthly》2002,11(1):1221-1224
The reactive 1:1 intermediate produced in the reaction between alkyl isocyanides and ethynyl phenyl ketone was trapped with N,N ′-dimethylbarbituric acid to produce alkyl 1,3-dimethyl-2,4-dioxo-7-phenyl-1,3,4,5-tetrahydro-2H-pyrano[2,3-d]pyrimidine-5-carboxamides in good yields. 相似文献
19.
The reactivity and the synthetic potential of α-cyano-α-isocyanoalkanoates 2 were investigated. Interestingly, reaction of 2 with alkoxides gave (alkoxy)(alkyl)imidazoles 5 , whereas the analogous thiolates led to different products, namely substituted 4H-imidazoles 7 , together with compounds 6 , which formed by addition of thiolate to the isocyano group. Primary amines reacted, on one hand, in the same manner as thiolates to form of 4H-imidazoles 10 , and, on the other hand, cleavage of the molecule to the proposed unstable aminoimidazole 8 and the carbamate 9 was observed. Secondary amines add selectively to the isocyano group to form compounds 11 . Like simple isocyanides, α-cyano-α-isocyanoalkanoates 2 can be subjected to [4+1] cycloadditions and multicomponent reactions of the Passerini type. Mechanisms for the described reactions are discussed. 相似文献
20.
A convenient procedure for the synthesis of 2,N,N‐trisubstituted 1H‐indole‐1‐carbothioamides from 2‐(acylmethyl)phenyl isocyanides has been developed. Thus, these isocyanides are converted into (Z)‐ [1‐alkyl (or phenyl)‐2‐(2‐isothiocyanatophenyl)ethenyl] 1,1‐dimethylethyl carbonates via an easy two‐step sequence. Treatment with secondary amines gave thiourea intermediates which afforded with CF3COOH (TFA) the desired products in fair‐to‐good yields. 相似文献