Syntheses and structural characterizations of 2-pyridyl(N/O)spirocyclotriphosphazene derivatives

Elmas G.

PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS, cilt.194, sa.1-2, ss.13-24, 2019 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 194 Sayı: 1-2
  • Basım Tarihi: 2019
  • Doi Numarası: 10.1080/10426507.2018.1469490
  • Dergi Adı: PHOSPHORUS SULFUR AND SILICON AND THE RELATED ELEMENTS
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.13-24
  • Anahtar Kelimeler: 2-pyridyl(N, O)spirocyclotriphosphazenes, substitution reactions, spectroscopy, CSA, PHOSPHORUS-NITROGEN COMPOUNDS, DNA INTERACTIONS, STEREOGENIC PROPERTIES, BIOLOGICAL-ACTIVITIES, CYTOTOXIC ACTIVITIES, ELECTROCHEMICAL INVESTIGATIONS, ANTIMICROBIAL ACTIVITIES, CRYSTAL-STRUCTURES, ANTITUBERCULOSIS, MONO
  • Ankara Üniversitesi Adresli: Evet

Özet

The Cl exchange reaction of hexachlorocyclotriphosphazene, N3P3Cl6 (1), with one equimolar amount of sodium salt of N/O donor type bidentate ligand containing a 2-pyridyl pendant arm (2) afforded, regioselectively, the partly substituted 2-pyridyl(N/O)spirocyclotriphosphazene (3; with a yield of 65%) in THF. The reactions of 3 with excess pyrrolidine, morpholine and 1,4-dioxa-8-azaspiro[4,5]decane (DASD) led to the formation of the tetraamino-2-pyridyl(N/O)spirocyclotriphosphazenes (3a-3c) in high yields. Compound 3 also gave both tetrapiperidino (3d) and gem-bispiperidino (3e) products with excess piperidine. The structures of all the compounds were determined by elemental analyses, ESI-MS, FTIR, HSQC, HMBC and H-1, C-13, and P-31 NMR techniques. The crystal structure of 3c was identified by single crystal X-ray crystallography. Besides, the compound 3e had one stereogenic P atom, and its chirality was verified by P-31 NMR spectroscopy in the presence of (S)-(+)-2,2,2-trifluoro-1-(9'-anthryl)-ethanol (CSA).