Convenient method for the synthesis of C-phosphorylated N-arylformamidines

Marchenko, A. P.; Koidan, G. N.; Hurieva, Anastasiya; Merkulov, A. S.; Пинчук, А. M.; Yurchenko, A. A.; Kostyuk, Alexander

doi:10.1016/j.tet.2010.03.087

Cited by 9 publications

(7 citation statements)

References 15 publications

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“…In our previous work, we showed that the cyclization of C ‐phosphorylated N,N ‐dimethyl‐N′‐arylformamidines critically depends on the position and electron‐donating capability of substituents at the aryl ring (Scheme ). The cyclization proceeds with the elimination of dimethylamine and its mechanism was described in detail [6b]. Electron‐donating substituents at the meta position promoted cyclization the best.…”

Section: Resultsmentioning

confidence: 99%

“…C ‐phosphanyl( N ‐aryl)formamidines derived from 1,3‐diaminobenzene and 1,3,5‐triaminobenzene undergo intramolecular cyclocondensations furnishing tricyclic and tetracyclic azaphospholes, respectively. Interestingly, the double and the triple intramolecular cyclocondensations proceed more efficiently than formerly reported reaction involving monoaminobenzene derivatives . Therefore, a facile synthetic route to 1,3‐azaphospholes starting from 1,3‐diaminobenzene and 1,3,5‐triaminobenzene was developed.…”

Section: Discussionmentioning

confidence: 99%

“…The rate of the cyclization has been shown to depend on the benzene ring substituent electron‐donating efficiency. At the same time, the method tolerates various substituents . In this contribution, we describe the extension of the method to 1,3‐diaminobenzene and 1,3,5‐triaminobenzene to prepare polycyclic 3 H ‐1,3‐benzazaphospholes.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of Bis‐ and Tris(3‐H‐1,3‐azaphospholo)benzenes

Marchenko

Koidan

Huryeva

et al. 2013

Heteroatom Chemistry

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The previously developed intramolecular cyclocondensation of C‐phosphanyl(N‐aryl)formamidines into 3‐H‐1,3‐benzazaphospholes has been successfully extended to 1,3‐diaminobenzene and 1,3,5‐triaminobenzene. Its condensation presents the way to tricyclic and tetracyclic azaphospholes. Their structures were confirmed by spectroscopic methods and key tricyclic and tetracyclic compounds were further characterized by single crystal X‐ray diffraction.

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Section: Resultsmentioning

confidence: 99%

Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Synthesis of Bis‐ and Tris(3‐H‐1,3‐azaphospholo)benzenes

Marchenko

Koidan

Huryeva

et al. 2013

Heteroatom Chemistry

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“…Thus, it was shown that the treatment of pentavalent derivatives like CCl 3 PX(NHAr)R where X=O, S, Se with dimethylamine gave P V formamidines. The method allows preparation of P III derivatives via reduction of the corresponding P V (X=Se) derivatives [6,7] (Figure 1).…”

Section: Introductionmentioning

confidence: 99%

Polydentate Phosphane Ligands Featuring N,N,N’‐Trialkylformamidines

et al. 2021

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A set of novel polydentate phosphanes featuring one, two and three formamidine substituents was prepared by the reaction of C‐trimethylsilyl N,N,N’‐trialkylformamidines with P(III) chlorides. Chloro‐ and dichlorophosphanes gave tertiary phosphanes. More sterically congested adamantyldichlorophosphane reacted only with the least sterically congested silylformamidine. With phosphorus trichloride, five‐membered heterocycles, namely 1,4,2‐diazaphosphol‐4‐ium chlorides were formed in most cases. A mechanism for the formation of diazaphospholes was proposed and corroborated by DFT calculations. A key chlorophosphane underwent 1,2‐phosphorus shift giving the corresponding carbene that readily cyclized into diazaphospholium salts. The key compounds were studied by X‐ray diffractometry. Analysis of molecular structures of 1,4,2‐diazaphosphol‐4‐ium chloride 13 c and 1H‐1,4,2‐diazaphosphole 14 c revealed that the N‐Cring bonds for the orthogonally oriented i‐propylamino groups are unusually short. Only in the case of N,N‐dimethyl‐N’‐isopropyltrimethylsilylformamidine, we managed to isolate trisphosphane, albeit in a low yield.

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“…18 Because of the pyramidal preference of σ 3 ,λ 3 -phosphorus, the P lone pair in phospholes usually has little participation in cyclic electron delocalization. 19 The synthesis of the monocyclized azaphosphole-ferrocenes Se- (10) and 10 was conducted following minor modifications of the general route developed for bis-azadiphospholeferrocenes Se-(7) and 7, as described in Scheme 4.…”

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confidence: 99%