Facile synthesis of novel 7-aminofuro- and 7-aminothieno[2,3-d]pyridazin-4(5H)-one and 4-aminophthalazin-1(2H)-ones

KOZA, GANİ; KESKİN, SELBİ; ÖZER, Merve Sinem; Cengiz, Betul; Şahin, Ertan; BALCI, Metin

doi:10.1016/j.tet.2012.10.010

Makale Tam Makale Uluslararası 2013

Facile synthesis of novel 7-aminofuro- and 7-aminothieno[2,3-d]pyridazin-4(5H)-one and 4-aminophthalazin-1(2H)-ones

GANİ KOZA, SELBİ KESKİN, Merve Sinem ÖZER, Betul Cengiz, Ertan Şahin, Metin BALCI

TETRAHEDRON Cilt 69 · Sayı 1 · ss. 395–409 · 01.01.2013

DOI ile aç

Özet

We hereby report the synthesis of a novel class of compounds, 7-aminofuro- and 7-aminothieno[2,3-d]pyridazin-4(5H)-one and 4-aminophthalazin-1(2H)-ones starting from methyl 2-(2-methoxy-2-oxoethyl)furan- and thiophene-3-carboxylate and methyl 2-(2-methoxy-2-oxoethyl)benzoate. The ester functionalities connected directly to the aromatic ring were regiospecifically converted to the acid, whereas methylene groups were oxidized to the corresponding ketoesters. Reaction of the ketoesters with hydrazine provided the hydrazone derivatives. An intramolecular cyclization in the presence of thionyl chloride formed a fused pyridazinone skeleton. Hydrolysis of the remaining ester groups and transformation of the acid functionalities to the acyl azides followed by Curtius rearrangement gave the isocyanates. Reaction of the isocyanates with methanol and water produced urethane and amino-pyridazinone derivatives, respectively. (C) 2012 Elsevier Ltd. All rights reserved.

Anahtar kelimeler

INHIBITORS Pyridazinone Furopyridazinone Thienopyridazinone Phthalazinone Acyl azide Curtius rearrangement PALLADIUM-CATALYZED SYNTHESIS CARDIOTONIC AGENTS BENZAL)HYDRAZONE DERIVATIVES RECEPTOR ANTAGONISTS HOMOPHTHALIC ACID PART 10 PYRIDAZINES SKELETON CONSTRUCTION

Atıf için künye

KOZA, G., KESKİN, S., ÖZER, M. S., Cengiz, B., Şahin, E., & BALCI, M. (2013). Facile synthesis of novel 7-aminofuro- and 7-aminothieno[2,3-d]pyridazin-4(5H)-one and 4-aminophthalazin-1(2H)-ones. TETRAHEDRON, 69(1), 395–409. https://doi.org/10.1016/j.tet.2012.10.010

BibTeX

@article{koza2013-66557,
  author = {KOZA, GANİ and KESKİN, SELBİ and ÖZER, Merve Sinem and Cengiz, Betul and Şahin, Ertan and BALCI, Metin},
  title = {Facile synthesis of novel 7-aminofuro- and 7-aminothieno[2,3-d]pyridazin-4(5H)-one and 4-aminophthalazin-1(2H)-ones},
  journal = {TETRAHEDRON},
  year = {2013},
  volume = {69},
  number = {1},
  pages = {395--409},
  issn = {0040-4020},
  doi = {10.1016/j.tet.2012.10.010},
  url = {https://akademik.atauni.edu.tr/yayinlar/66557-facile-synthesis-of-novel-7-aminofuro-and-7-aminothieno23-dpyridazin-45h-one-and}
}