C-acylation of electron-rich heterocyclic compounds with Kirsanov isocyanate

Толмачев, А. А.; Chaikovskaya, A. A.; Smaliy, Radomyr V.; Kudrya, T. N.; Yurchenko, A. A.; Пинчук, А. M.

doi:10.1002/(sici)1098-1071(1999)10:4<343::aid-hc14>3.0.co;2-c

Cited by 9 publications

(5 citation statements)

References 4 publications

(6 reference statements)

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“…The products 12 and 13 were isolated in high yields (70-99%). They are of interest due to the presence of biologically active Het-moieties and were used as intermediates for heterocycles with carbamoyl-14 and cyano-substituents 15 (Scheme 9) [21][22][23][24].…”

Section: Methodsmentioning

confidence: 99%

N-Acylamidophosphinates: Structure, Properties and Complexation Towards Main Group Metal Cations

Sokolov¹,

Brusko²,

Zabirov³

et al. 2006

COC

104

138

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N-Acylamidophosphinates RC(X)NHP(Y)R' 2 (NAAP) and their thioanalogues (X,Y= O, S; R = Alk, Ar, CCl 3 , Het, NR 2 2 , NR 2 R 3 ; R ' = Ar, OAlk, OAr, SAlk, NAlk 2 , NHAr) contain X, Y donor atoms and amide nitrogen, which are capable of taking in complexation with metal cations. An application of NAAP complexes in supramolecular chemistry has been investigated in the last decades. Developed synthetic methods allow us to obtain N-acylamidophosphinate ligands contained multiple chelating groups or a combination of several essentially various coordinating fragments in the molecule: chelating moiety C(X)NHP(Y) and a macrocycle. The latter ligands are capable of connecting ions simultaneously by the chelating sites, and by the "guest-host" mechanism using the macrocycle. The bibliography includes 104 references.Investigation of complexing properties of conjugated organophosphorous anions is an important issue of modern coordination and organoelement chemistry [1,2]. The application of NMR, IR and UV spectroscopic methods to study the structure and dynamic processes in solutions of such compounds allows to investigate the nature of the chemical bonds in the conjugated organophosphorous anions and opens the way for the creation of new types of selective complexing agents.N-Acylamidophosphates, N-acylamidophosphinates and their thioanalogues with common formula RC(X)NHP(Y)R`2 (NAAP) contain X, Y donor atoms and an amido nitrogen atom which can be involved in complexation (Scheme 1). In terms of reactivity NAAP are quite different from each other depending on the nature and combination of atoms X and Y in the molecule, as well as the nature of substituents of (thio)carbonyl and (thio)phosphoryl moieties. Scheme 1.

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Section: Methodsmentioning

confidence: 99%

N-Acylamidophosphinates: Structure, Properties and Complexation Towards Main Group Metal Cations

Sokolov¹,

Brusko²,

Zabirov³

et al. 2006

COC

104

138

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“…The chemical shifts of other protons of the carboxamide moiety appeared in the expected regions. 18 It is of further interest to observe that the protons of the carboxamide function resonated downfield, when compared to the corresponding protons in the free heterocycles. The NH proton signals were confirmed by D 2 O exchange experiments.…”

Section: Chartmentioning

confidence: 88%

“…18 Cyclocondensation of 2 in situ with 3,4-diamino-1,2,5-oxadiazole (3) 19 in the presence of triethylamine at 50-60 °C in octane, yielded the title compounds (4-13). Thin layer chromatography (TLC) was employed to follow the progress of the reaction and purity of the products.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and antimicrobial activity of novel 2-(heteryl-carboxamido)-2,3-dihydro-1H-1,2,5-oxadiazolo[3,4-c] [1,3,2]diazaphosphole-2-oxides

Babu¹,

Kumar²,

Srinivasulu³

et al. 2007

Arkivoc

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Some novel 2-(heterylcarboxamido)-2,3-dihydro-1H-1,2,5-oxadiazolo [3,4-c][1,3,2]diazaphosphole-2-oxides (4-13) have been synthesized from reaction of 3,4-diamino-1,2,5-oxadiazole (3) with various dichlorophosphinylcarboxamides (2), which were prepared by C-acylation of electron-rich heterocyclic compounds with dichloro isocyanato phosphine oxide (Kirsanov isocyanate) (1) in dry octane, in the presence of triethylamine at 50-60 °C. Their structures were determined by IR, 1 H, 13 C, 31 P NMR and mass spectral (MS) studies. They were screened for antifungal and antibacterial activity against Curvularia lunata / Aspergillus niger and Staphylococcus aureus / Escherichia coli, respectively. Most of these compounds exhibited moderate activity in the assays.

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“…). The literature analysis shows that these ligands are poorly represented by the pyrrole derivatives, whereas the well‐known property of pyrroles is easy direct—phosphorylation by phosphorus halides and good reactivity in other reactions of electrophilic substitution . This work presents an attempt to reach the precursors of the mentioned type of ligands by formylation of substituted phosphorylated pyrroles.…”

Section: Introductionmentioning

confidence: 99%