Synthesis of 2-aryl-1,2,3,4-tetrahydroquinazolin-1-ols and their conversion to 7-aryl-9H-6-oxa-5,8-diaza-benzocycloheptenes

Coskun N., Cetin M.

TETRAHEDRON LETTERS, cilt.45, sa.49, ss.8973-8975, 2004 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 45 Sayı: 49
  • Basım Tarihi: 2004
  • Doi Numarası: 10.1016/j.tetlet.2004.10.062
  • Dergi Adı: TETRAHEDRON LETTERS
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.8973-8975
  • Anahtar Kelimeler: quinazoline, quinazolin-1-ol, 6-oxa-5,8-diaza-benzocycloheptenes, benzo[c]oxadiazepine, ring expansion, oxidation with H(2)O(2-)tungstate, rearrangement, ACRIDONE ALKALOIDS, QUINAZOLINE, QUINOLINE, INHIBITORS
  • Bursa Uludağ Üniversitesi Adresli: Evet

Özet

2-Aminobenzylamine was reacted with corresponding aromatic or heteroaromatic aldehydes to give 1,2,3,4-tetrahydroquinazolines 1 the oxidation of which with H2O2-tungstate in methanol led to the formation of the corresponding 1,2,3,4-tetrahydroquinazolin-1-ols 2. A one-pot procedure involving the treatment of the in situ formed quinazoline 1 with H2O-tungstate again led to the formation of 2. Compounds 2 react with 2equiv of aryl isocyanate in toluene at room temperature to produce compounds 3. The probable mechanism of the ring-expanding carbamoylation of quinazolin-1-ols 2 to 6-oxa-5,8-diaza-benzocycloheptenes 3 is discussed. (C) 2004 Elsevier Ltd. All rights reserved.