One-Pot Synthesis of Fused Pyridazino[4,5-b][1,4]oxazepine-diones via Smiles Rearrangement

被引:21
作者
Liu, Yanli [1 ]
Ma, Ying [1 ]
Zhan, Chunjing [1 ]
Huang, Aiping [1 ]
Ma, Chen [1 ,2 ]
机构
[1] Shandong Univ, Sch Chem & Chem Engn, Jinan 250100, Peoples R China
[2] Peking Univ, State Key Lab Nat & Biomimet Drugs, Beijing 100191, Peoples R China
基金
美国国家科学基金会;
关键词
pyridazino[4,5-b][1,4]oxazepine-dione; one-pot; synthesis; Smiles rearrangement; tandem reaction; 5-HT1A RECEPTOR AGONISTS; DERIVATIVES; INHIBITORS;
D O I
10.1055/s-0031-1290073
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Fused pyridazino[4,5-b][1,4]oxazepine-diones were easily obtained in moderate to excellent yields via Smiles rearrangement. The synthetic approach is supported by a one-pot coupling-Smiles rearrangement-cyclization process. This process has potential applications in the synthesis of biologically and medicinally relevant compounds.
引用
收藏
页码:255 / 258
页数:4
相关论文
共 29 条
[1]  
Arif Jamal M, 2006, Asian Pac J Cancer Prev, V7, P249
[2]   Enantiomeric separation of optically active pyridazinone derivatives by chiral HPLC [J].
Bidló-Iglóy, M ;
Mátyus, P .
JOURNAL OF PHARMACEUTICAL AND BIOMEDICAL ANALYSIS, 1999, 19 (3-4) :487-490
[3]   New anilinophthalazines as potent and orally well absorbed inhibitors of the VEGF receptor tyrosine kinases useful as antagonists of tumor-driven angiogenesis [J].
Bold, G ;
Altmann, KH ;
Frei, J ;
Lang, M ;
Manley, PW ;
Traxler, P ;
Wietfeld, B ;
Brüggen, J ;
Buchdunger, E ;
Cozens, R ;
Ferrari, S ;
Furet, P ;
Hofmann, F ;
Martiny-Baron, G ;
Mestan, J ;
Rösel, J ;
Sills, M ;
Stover, D ;
Acemoglu, F ;
Boss, E ;
Emmenegger, R ;
Lässer, L ;
Masso, E ;
Roth, R ;
Schlachter, C ;
Vetterli, W ;
Wyss, D ;
Wood, JM .
JOURNAL OF MEDICINAL CHEMISTRY, 2000, 43 (12) :2310-2323
[4]   Novel synthesis of pyridazino[4,5-b][1,4]oxazin-3,8-diones [J].
Cho, SD ;
Song, SY ;
Park, YD ;
Kim, JJ ;
Joo, WH ;
Shiro, M ;
Falck, JR ;
Shin, DS ;
Yoon, YJ .
TETRAHEDRON LETTERS, 2003, 44 (50) :8995-8998
[5]   Vasorelaxant activity of phthalazinones and related compounds [J].
del Olmo, E ;
Barboza, B ;
Ybarra, MI ;
López-Pérez, JL ;
Carrón, R ;
Sevilla, MA ;
Boselli, C ;
Feliciano, AS .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2006, 16 (10) :2786-2790
[6]   Design and synthesis of 10-alkoxy-5, 6-dihydro-triazolo[4,3-d]benzo[f][1,4] oxazepine derivatives with anticonvulsant activity [J].
Deng, Xian-Qing ;
Wei, Cheng-Xi ;
Li, Fu-Nan ;
Sun, Zhi-Gang ;
Quan, Zhe-Shan .
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2010, 45 (07) :3080-3086
[7]   Theoretical and experimental studies on ring closure reactions of 4(5)-chloro-5(4)-hydroxyalkylamino-6-nitro-3 (2H)-pyridazinones [J].
Eliás, O ;
Károlyházy, L ;
Stájer, G ;
Fülöp, F ;
Czakó, K ;
Harmath, V ;
Barabás, O ;
Keseru, K ;
Mátyus, P .
JOURNAL OF MOLECULAR STRUCTURE-THEOCHEM, 2001, 545 :75-96
[8]  
Fukui H., 2001, Patent No. [WO 0155121, 0155121]
[9]   Synthesis, SAR studies, and evaluation of 1,4-benzoxazepine derivatives as selective 5-HT1A receptor agonists with neuroprotective effect:: Discovery of Piclozotan [J].
Kamei, K ;
Maeda, N ;
Nomura, K ;
Shibata, M ;
Katsuragi-Ogino, R ;
Koyama, M ;
Nakajima, M ;
Inoue, T ;
Ohno, T ;
Tatsuoka, T .
BIOORGANIC & MEDICINAL CHEMISTRY, 2006, 14 (06) :1978-1992
[10]   New 5-HT1A receptor agonists possessing 1,4-benzoxazepine scaffold exhibit highly potent anti-ischemic effects [J].
Kamei, K ;
Maeda, N ;
Ogino, R ;
Koyama, M ;
Nakajima, M ;
Tatsuoka, T ;
Ohno, T ;
Inoue, T .
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 2001, 11 (04) :595-598