New route for synthesis of 2-(2,2-dimethoxyethyl)-1,2,3,4,5,6-hexahydro-1,5-methanoazocino[4,3-b] indole and DFT investigation

ULUDAĞ N., SERDAROĞLU G.

HELIYON, cilt.6, sa.6, 2020 (ESCI) identifier identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 6 Sayı: 6
  • Basım Tarihi: 2020
  • Doi Numarası: 10.1016/j.heliyon.2020.e04105
  • Dergi Adı: HELIYON
  • Derginin Tarandığı İndeksler: Emerging Sources Citation Index (ESCI), Scopus, CAB Abstracts, Veterinary Science Database, Directory of Open Access Journals
  • Anahtar Kelimeler: Theoretical chemistry, Organic chemistry, Strychnos alkaloids, FT-IR, NMR, NLO, FMO, CONCISE TOTAL-SYNTHESIS, SPECTROSCOPIC FT-IR, HOMO-LUMO, OPTICAL-PROPERTIES, NMR, NLO, NBO, MEP, FMO, REDUCTION
  • Sivas Cumhuriyet Üniversitesi Adresli: Evet

Özet

Development of efficient sequences for the synthesis of the title compound (2-(2,2-dimethoxyethyl)-1,2,3,4,5,6-hexahydro-1,5-methanoazocino[4,3-b]indole) (7) was described. The title compound was synthesized through several steps starting from phenylhydrazine hydrochloride and dimethyl (R)-2-(3-oxocyclohexyl)malonate. In this route, all synthesized compounds were observed by spectroscopic tools (FT-IR, NMR): Methyl-2-(2,3,4,9-1H-carbazol-2-yl)acetate (3), 2-(2,3,4,9-tetrahydro-1H-carbazol-2-yl)acetic acid (4), N-(2,2-dimedioxyethyl)-2-(2,3,4,9-tetrahydro-1H-carbazol-2-yl)acetamide (5), 2-(2,2-ctimethoxyethyl)-1,2,4,5,6,7-hexahydro-3H-1,5-mediatioazocino[4,3-b]indol-3-one (6), 2-(2,2-dimethax-yethyl)-2,3,4,5,6,7-hocahydro-1H-1,5-methanoazocino[4,3-b]indole (7). The central step in these syntheses is the dehydrogenative reaction, which constructs the tetracyclic ring system from a much simpler tetracyclic precursor. The six-stable conformers of the compound (r were used for further calculations such as FT-IR, NMR, NLO, and FMO analyses, performed at the B3LYP/6-311++G(d,p) level. This work revealed that (7) can be a good material to use in the non-linear optical material because its beta tensor is greater ten times than that of the urea.