Isocyanatophosphoryl Dichloride as Reagent for Introduction of Carbamoyl Group into Molecules of π-Excessive Heterocycles and Enamines

Smaliy, Radomyr V.; Chaikovskaya, A. A.; Пинчук, А. M.; Толмачев, А. А.

doi:10.1055/s-2003-42404

Cited by 9 publications

(8 citation statements)

References 3 publications

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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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“…For background to the chemistry of phosphorus-organic compounds, see: Ly & Woollins (1998). For details of the synthesis and properties of the [(1,3-thiazol-2-ylamino)carbonyl]phosphoramidic acid, see: Kirsanov & Levchenko (1957); Smaliy et al(2003). For structural analogues of phosphorylated carbacylamides and their properties, see: Amirkhanov et al (1997).…”

Section: Related Literaturementioning

confidence: 99%

“…The synthesis of [(1,3-thiazol-2-ylamino)carbonyl]phosphoramidic acid (II) was carried out according to the method described by Kirsanov (Kirsanov & Levchenko, 1957). The compound N-1,3-thiazol-2-yl-urea phosphate (I) was obtained due to hydrolyzation of (II) in the water solution (Smaliy et al, 2003). The crystals (I) suitable for X-ray analysis were obtained by heating of [(1,3-thiazol-2-ylamino)carbonyl]phosphoramidic acid in water and evaporating the solvent at room temperature for about 2 days.…”

Section: S2 Experimentalmentioning

confidence: 99%

2-Ureido-1,3-thiazol-3-ium dihydrogen phosphate

et al. 2011

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The title compound, C4H6N3OS+·H2PO4 −, (I), was obtained as a result of hydrolysis of [(1,3-thiazol-2-ylamino)carbonyl]phosphoramidic acid, (II), in water. X-ray analysis has shown that the N—P bond in (II) breaks, leading to the formation of the substituted carbamide (I). This compound exists as an internal salt. The unit cell consists of a urea cation and an anion of H2PO4 −. Protonation of the N atom of the heterocyclic ring was confirmed by the location of the H atom in a difference Fourier map. The molecules of substituted urea are connected by O⋯O hydrogen bonds into unlimited planes. In turn, those planes are connected to each other via N—H⋯O hydrogen bonds with molecules of phosphoric acid, forming a three-dimensional polymer.

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“…31 Benzyl or cyanoethyl phosphochloroamidites (64) and (65) and D-mannose (66) are convenient starting materials for the preparation of a wide range of a-D mannosylphosphate serine derivatives (67) a new class of synthetic glucopeptides (Scheme 11). 32 Three 1-(2-nitrophenyl)ethyl phosphoroamino acid building blocks (68), (69) and (70) for solid-phase peptide synthesis have been described ( Figure 17). 32 Three 1-(2-nitrophenyl)ethyl phosphoroamino acid building blocks (68), (69) and (70) for solid-phase peptide synthesis have been described ( Figure 17).…”

Section: Figure 15mentioning

confidence: 99%

Organophosphorus Chemistry

Hall

Bricklebank

Grampel³

et al. 2006

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Organophosphorus compounds are ubiquitous in nature, and due to their innate chemical properties, serve a fundamental role in a number of important fields. Among the more prominent features that elevate their status as a unique and versatile class of compounds, include variable oxidation states, multivalency, asymmetry and metal-binding properties. Their presence in bioactive natural products, endogenous biomolecules, small molecule therapeutic agents and pro-drugs substantiates their role in modern synthetic chemistry and chemical biology. Moreover, their central use as ligands and effectors in asymmetric catalysis, as well as key functional groups for the development of new synthetic methods, has taken the field to new heights. This Thematic Series highlights and details some of the novel methods that are advancing the field of organophosphorus chemistry.The Thematic Series covers topics that range from new synthetic methods and phosphorus-based ligands in asymmetric catalysis to bisphosphonates as promising enzyme inhibitors. More specifically, the Thematic Series spans new methods in C-P bond formation, chiral phosphines in nucleophilic organocatalysis, chiral N-phosphinyl auxiliaries, cyclic phosphonamide reagents in the total synthesis of natural products, phosphinate-containing heterocycles, new routes to phosphinoyl-indoles and phosphinoyl-isocoumarins and new chemistries of H-phosphonates. The Thematic Series also details work on new metathesis-based reactions of vinyl phosphonates and phosphate tethers, novel phosphorus-based ligands in asymmetric catalysis, novel rasta resin-triphenylphosphine oxides and their use as recyclable heterogeneous reagents, the Atherton-Todd reaction, cyclic phosphonium ionic liquids with distinct properties, photo-removable phosphate protecting groups, new methods of C-H functionalization using phosphoryl-related directing groups, the exciting chemistry of substituted phosphanylidenecarbenes and phosphoryl azides, and bisphosphonate ethers as promising inhibitors of geranylgeranyl diphosphate synthase (GGDPS).The articles and reviews capture the emerging potential of organophosphorus compounds and exciting opportunities in the field, and hopefully, will inspire and motivate investigators in the field to investigate new chemistry in this area. Taken collectively, organophosphorus chemistry embodies a broad, vibrant and continual growing scientific area with this Thematic Series highlighting recent advances in the field. We are grateful and indebted to the authors for their hard work and exciting contri-

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Isocyanatophosphoryl Dichloride as Reagent for Introduction of Carbamoyl Group into Molecules of π-Excessive Heterocycles and Enamines

Cited by 9 publications

References 3 publications

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

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

2-Ureido-1,3-thiazol-3-ium dihydrogen phosphate

Organophosphorus Chemistry

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