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1.
Azeto[1,2-a]imidazoles are prepared by a formal intramolecular [2+2] cycloaddition of imino-ketenimines in which an ethylene chain is linking the nitrogen atoms of both functionalities, bearing a methyl and a phenyl group on the terminal carbon atom of the heterocumulene. By acid-catalyzed hydrolysis these azeto[1,2-a]imidazoles are converted into 6,6,7-trisubstituted hexahydro-1,4-diazepin-5-ones, which have been alternatively prepared via intramolecular transamidation of N-(2-aminoethyl)-β-lactams. 相似文献
2.
The thermal treatment of N-(2-propenyl)-1-naphthylamines provided the expected aza-Claisen rearranged products, 2-(2-propenyl)-1-naphthylamines and benz[g]indoles, these last derived from an intramolecular hydroamination reaction on those primary products. The 2-(2-propenyl)-1-naphthylamines were converted into their triphenylphosphazene derivatives, which by aza-Wittig reaction with disubstituted ketenes yielded N-[2-(2-propenyl)-1-naphthyl] ketenimines. The heating of these ketenimines in boiling toluene induced their cyclization either via an intramolecular Diels-Alder reaction, to afford dibenz[b,h]acridines, or via [1,5] hydrogen migration from the sp3 carbon atom of the propenyl substituent to the central carbon atom of the ketenimine fragment, followed by a 6π electrocyclic ring closure, to give benzo[h]quinolines. 相似文献
3.
Issa?YavariEmail author Hoorieh?Djahaniani Farough?Nasiri 《Monatshefte für Chemie / Chemical Monthly》2004,135(5):543-548
Summary. The 1:1 reactive intermediate generated by the addition of alkyl isocyanides to dialkyl acetylenedicarboxylates was trapped by fairly strong NH-acids such as carbazole, indole, or pyrrole to yield highly functionalized 1-azadienes and ketenimines. 相似文献
4.
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
5.
I. Yavari M. Davar-Panah M. Heydari K. Najafian A. Zonouzi 《Monatshefte für Chemie / Chemical Monthly》1996,127(8-9):963-966
Summary A one-pot synthesis of highly functionalized ketenimines by reaction of alkyl isocyanides with dialkyl acetylenedicarboxylates in presence of 1,3-diphenylpropan-1,3-dione is reported.
Ein einfacher Weg zu hochfunktionalisierten Keteniminen
Zusammenfassung Es wird eine Eintopfsynthese hochfunktionalisierter Ketenimine durch Reaktion von Isocyaniden mit Dialkylacetylendicarboxylaten in Gegenwart von 1,3-Diphenylpropan-1,2-dion beschrieben.相似文献
6.
Three-component reaction of alkyl isocyanides and dialkyl acetylenedicarboxylates in the presence of 2,2,2-trifluoro-N-aryl-acetamides in dichloromethane at ambient temperature afforded dialkyl 2-(N-(aryl)-2,2,2-trifluoroacetamido)-3-(alkylimino) methylene-succinate derivatives in excellent yields. 相似文献
7.
A one-pot synthesis of 4(3H)-quinazolinones from terminal alkynes, sulphonyl azide, o-iodoanilines, and carbon monoxide has been developed. This cascade process includes the copper-catalyzed three-component reaction of alkyne, azide and amine, the palladium-catalyzed carbonylation, and the Lewis acid catalyzed hydrolysis of sulfonamide. 相似文献
8.
Michael Schmittel Jens-Peter Steffen Miguel . Wencesla ngel Bernd Engels Christian Lennartz Michael Hanrath 《Angewandte Chemie (International ed. in English)》1998,37(11):1562-1564
Both benzocarbazoles and quinolines can be synthesized from enyne ketenimines 1 generated in situ via biradical intermediates (see reaction below). Which of the heterocyclic ring systems is formed depends on the choice of the substituent R1 at the alkyne terminus. 相似文献
9.
Mateo AlajarinMarta Marin-Luna Maria-Mar OrtinPilar Sanchez-Andrada Angel Vidal 《Tetrahedron》2011,67(31):5590-5595
N[β-(Hetero)arylvinyl] ketenimines and carbodiimides bearing adequately positioned 1,3-dioxolane functions experience a new class of tandem process consisting of a 6π electrocyclic ring closure followed by a rare retro-cheletropic ene reaction, the extrusion of 2-carbena-1,3-dioxolane. This mechanistic sequence is supported by a computational study using DFT methods, showing that the simultaneous recovery of aromaticity at two rings is the clue for the low energy barrier of the retro-cheletropic step. Moreover, the highly exergonic decomposition of 2-carbena-1,3-dioxolane into CO2 plus ethylene contribute to the success of the tandem sequences. 相似文献
10.
Rudolf Aumann 《Angewandte Chemie (International ed. in English)》1988,27(11):1456-1467
Ketenimine complexes are readily available in great variety by reaction of isocyanides with carbene complexes. They have proven to be useful building blocks in new synthetic approaches to carbocyclic and N-heterocyclic four-, five-, and six-membered rings. The reactions involve new metal-induced bond formation patterns of the ketenimine ligands, which can be influenced across a wide range by varying the following five parameters: the metal, the ligands, and the three substituents on the N?C?C unit. 相似文献