Studies on nitrogen-containing heterocyclic compounds. Novel synthesis of naphtho[1,2-b and 2,1-b][1,8]naphthyridines and oxidation reactions with peroxy acids

被引：7
|
作者：
Takeuchi, I
Asai, K
Hamada, Y
Masuda, H
Suezawa, H
Hirota, M
Kurono, Y
Hatano, K
机构：
[1] YOKOHAMA NATL UNIV,FAC ENGN,DEPT SYNTHET CHEM,HODOGAYA KU,YOKOHAMA,KANAGAWA 240,JAPAN
[2] NAGOYA CITY UNIV,FAC PHARMACEUT SCI,MIZUHO KU,NAGOYA,AICHI 467,JAPAN
来源：
HETEROCYCLES | 1996年 / 43卷 / 10期
关键词：
D O I：
10.3987/COM-96-7525
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A modified Friedlander condensation of 2-aminonicotinaldehyde with alpha- and beta-naphthols lead successfully to two new naphtho[1,2-b and 2,1-b][1,8]-naphthyridines in a single synthetic procedure. The oxidation of the naphthonaphthyridines with peroxy acids afforded novel products such as a seven-membered oxazepine moiety. Structures were characterized by standard spectroscopy. The crystal and molecular structures (3) and (4) were determined by X-ray analyses.
引用
收藏
页码：2139 / 2152
页数：14
相关论文
共 50 条
  • [1] Studies on nitrogen-containing heterocyclic compounds. Synthesis of benzo[b][1,8]naphthyridine and its oxidation reactions with peroxy acid
    Takeuchi, I
    Naga, N
    Kariyama, T
    Hamada, Y
    Matsuzaki, H
    HETEROCYCLES, 1998, 48 (10) : 2125 - 2132
  • [2] Design and synthesis of novel heterocyclic building blocks based on benzo[1,2-b:4,5-b′] and Naphtho[ 2,1-b:6,5-b′]chalcogenophenes
    Jeffries-El, Malika
    Muller, Evan
    Brown, Amy
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2017, 254
  • [3] Synthesis of naphtho[1,2-b]-, naphtho[2,1-b]-, and naphtho[2,3-b]azepinones via proton-induced cyclization of N-1(2)-naphthyl styrylacetamides
    Danyliuk, Ivanna Y.
    Vaskevych, Ruslan, I
    Vaskevych, Alla, I
    Suikov, Sergii Y.
    Rusanov, Eduard B.
    Chornous, Vitalij O.
    Vovk, Mykhailo V.
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2020, 57 (01) : 317 - 326
  • [4] CONFORMATIONAL-ANALYSIS AND PHOTOCHEMICAL BEHAVIOR OF SULFOXIDES IN THE NAPHTHO[1,2-B]THIOPYRAN AND NAPHTHO[2,1-B]THIOPYRAN SERIES
    STILL, IWJ
    ARORA, PC
    HASAN, SK
    KUTNEY, GW
    LO, LYT
    TURNBULL, K
    CANADIAN JOURNAL OF CHEMISTRY-REVUE CANADIENNE DE CHIMIE, 1981, 59 (02): : 199 - 209
  • [5] NAPHTHOTHIOPHENES .3. PREPARATION OF 4-NAPHTHO[1,2-B]THIOPHENEMETHANOLS AND 5-NAPHTHO[1,2-B]THIOPHENEMETHANOLS AND ATTEMPTS TO PREPARE 5-NAPHTHO[2,1-B]THIOPHENEMETHANOLS AS ANTIMALARIALS
    DAS, BP
    CUNNINGHAM, RT
    BOYKIN, DW
    JOURNAL OF MEDICINAL CHEMISTRY, 1973, 16 (12) : 1361 - 1365
  • [6] NITRILES IN HETEROCYCLIC SYNTHESIS - NOVEL SYNTHESES OF BENZO[B]PYRANS, NAPHTHO[1,2-B]PYRANS, NAPHTHO[2,1-B]PYRANS, PYRANO[3,2-H]QUINOLINES AND PYRANO[3,2-C]QUINOLINES
    ELAGAMEY, AGA
    SAWLLIM, SZ
    ELTAWEEL, FMA
    ELNAGDI, MH
    COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 1988, 53 (07) : 1534 - 1538
  • [7] Synthesis of novel nitrogen containing naphtho[2,1-b]furan derivatives and investigation of their anti microbial activities
    Nagaraja, Gundibasappa K.
    Prakash, Gowdara K.
    Kumaraswamy, Marlingaplara N.
    Vaidya, Vijayavittala P.
    Mahadevan, Kittappa M.
    ARKIVOC, 2006, : 160 - 168
  • [8] POSSIBLE ANTIFERTILITY COMPOUNDS .4. DIPHENYLNAPHTHOL[1,2-B]- AND DIPHENYLNAPHTHO(2,1-B]FURANS
    TIWARI, SS
    SRIVASTA.SC
    JOURNAL OF MEDICINAL CHEMISTRY, 1967, 10 (05) : 983 - +
  • [9] SYNTHESIS OF SOME NAPHTHO [2,1-b] FURO [3,2-d] PYRIMIDINES, NAPHTHO [2,1-b] FURO [3′,2′:4,5] PYRIMIDO [1,2-b] BENZO (d) THIAZOLE AND THEIR ANTIMICROBIAL ACTIVITY
    Rajashekhar, H.
    Ramesh, D.
    Chandrashekhar, C.
    Mahadevan, K. M.
    Vaidya, V. P.
    INDIAN JOURNAL OF HETEROCYCLIC CHEMISTRY, 2009, 18 (03) : 205 - 210
  • [10] An Efficient and Direct Solvent-Free Synthesis of Naphtho[1,2-b]furans, Naphtho[2,1-b]furans, and Furo[3,2-c]chromenes
    Adib, Mehdi
    Mahdavi, Mohammad
    Bagherzadeh, Sharareh
    Bijanzadeh, Hamid Reza
    SYNLETT, 2009, (15) : 2542 - 2544
12345