Synthesis and Characterization of 8-(2-((Trimethylsilyl)ethynyl)phenylamino)-7H-naphtho[1,8-bc]acridin-7-one

被引：5
|
作者：
Li, Lidong [1 ]
Gomes, Clara S. B. [1 ]
Gomes, Pedro T. [1 ]
Duarte, M. Teresa [1 ]
机构：
[1] Univ Tecn Lisboa, Dept Engn Quim & Biol, Ctr Quim Estrutural, Inst Super Tecn, P-1049001 Lisbon, Portugal
来源：
SYNTHETIC COMMUNICATIONS | 2008年 / 38卷 / 24期
关键词：
Acenaphthenequinone; acridine; cyclization; heterocycle; 2-(trimethylsilylethynyl)aniline;
D O I：
10.1080/00397910802369539
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An unexpected heterocyclic cyclization reaction of acenaphthenequinone and 2-(trimethylsilylethynyl)aniline in the presence of p-toluenesulfonic acid is reported. A new heterocyclic aromatic compound, 8-(2-((trimethylsilyl)ethynyl)phenylamino)-7H-naphtho[1,8-bc]acridin-7-one, was synthesized as the sole isolated reaction product and characterized by elemental analysis; NMR, IR, and UV spectroscopies; mass spectrometry, and single-crystal x-ray diffraction.
引用
收藏
页码：4415 / 4425
页数：11
相关论文
共 50 条
  • [31] SIMPLIFIED ANALOGS OF LYSERGIC-ACID .7. DERIVATIVES OF 4-AMINO-5-OXO-2,2A,3,4-TETRAHYDRO-5H-NAPHTHO[1,8-BC]THIOPHENE
    CRAIG, JC
    HURT, SD
    JOURNAL OF ORGANIC CHEMISTRY, 1979, 44 (07): : 1113 - 1117
  • [32] Synthesis and Characterization of 1,4-Dibromo-5H-benzo[a]phenothiazin-5-one and 8,13-Dibromo-7H-naphtho[2,3-a]phenothiazin-7-one for Use as Novel Fingermark Visualisation Reagents
    Akar, Kiymet Berkil
    Bebek, Oguzhan
    Eran, Baris
    JOURNAL OF THE CHEMICAL SOCIETY OF PAKISTAN, 2024, 46 (03): : 313 - 322
  • [33] 7-mesityl-7H-dinaphtho[1,8-bc:1',2'-e]borinine: A boron-doped polycyclic aromatic hydrocarbon for organic light-emitting diodes by Si-B exchange
    Xia, Youfu
    Zou, Jingya
    Fan, Tiantian
    Li, Tao
    Zhang, Jinfang
    Ding, Yuqiang
    TETRAHEDRON LETTERS, 2022, 108
  • [34] THE REACTION OF 2-((TRIMETHYLSILYL)METHYL)-2H-TETRAZOLES WITH ALDEHYDES AND KETONES IN THE PRESENCE OF 1,8-DIAZABICYCLO [5.4.0]UNDEC-7-ENE
    Umemoto, Hideaki
    Onaka, Takuya
    Miki, Yasuyoshi
    Nakamura, Akira
    Maegawa, Tomohiro
    HETEROCYCLES, 2014, 89 (11) : 2545 - 2553
  • [35] The crystal structure of (2a′S, 2a1′S, 3R,5a′S, 7′R)-5-(furan-3-yl)-2a′, 2a1′-dihydroxy-7′-methyldecahydro-2H-spiro[furan-3, 6′-naphtho [1,8-bc]furan]-2, 2′(2a′H)-dione, C19H22O7
    Xu, Xin-Ke
    Li, Can-Jie
    Tan, Jin-Lin
    Zhao, Hai-Yue
    Lin, Qiang
    Li, Yao-Lan
    Zhang, Yu-Bo
    Wang, Guo-Cai
    ZEITSCHRIFT FUR KRISTALLOGRAPHIE-NEW CRYSTAL STRUCTURES, 2021, 236 (06): : 1359 - 1361
  • [36] HETEROCYCLIC 12-PI-SYSTEMS AND 14-PI-SYSTEMS .34. EXPERIMENTS ON THE REACTIVITY OF 2-PHENYL-5H-NAPHTHO[1,8-BC]FURAN-5-ONE (OXAPSEUDOPHENALENONE)
    NEIDLEIN, R
    BERNHARD, E
    LIEBIGS ANNALEN DER CHEMIE, 1979, (07): : 959 - 964
  • [37] CONDENSED 1,8-NAPHTHYRIDINES .7. SYNTHESIS OF 6H-INDENO[1,2-B][1,8]-NAPHTHYRIDIN-6-ONE
    REDDY, KR
    RAO, GR
    MOGILAIAH, K
    SREENIVASULU, B
    JOURNAL OF THE INDIAN CHEMICAL SOCIETY, 1987, 64 (07) : 443 - 444
  • [38] HETEROCYCLIC 12-PI-SYSTEMS AND 14-PI-SYSTEMS .36. SYNTHESIS AND REACTIVITY OF 3-HYDROXY-2H-NAPHTHO[1,8-BC]THIOPHEN-2-ONE - ISO-PI-ELECTRONIC PERI-9-HYDROXYPHENALEN-1-ONE
    NEIDLEIN, R
    SEGUILCAMARGO, L
    LIEBIGS ANNALEN DER CHEMIE, 1979, (07): : 965 - 972
  • [39] An enantioselective synthesis of (R)- and (S)-3-amino-7-methyl-3,4-dihydro-1H-[1,8]naphthyridin-2-one
    Badland, Matthew
    Carroll, Robert
    Chadwick, Claire
    Cheung, Joe WaiChiu
    Fussell, Steve
    Laity, Daniel
    Peach, Philip
    Shaw, David
    TETRAHEDRON-ASYMMETRY, 2011, 22 (12) : 1328 - 1331
  • [40] Efficient One-Pot Syntheses of 7-Alkyl-6H, 7H-naphtho[1,2:5,6]pyrano-[3,2-c]chromen-6-ones by 1-Methyl-3-(2-(sulfooxy)ethyl)-1H-imidazol-3-ium Chloride
    Wan, Yu
    Wang, Chao
    Wang, Hai-ying
    Zhao, Ling-ling
    Zhang, Xiao-xiao
    Shi, Jing-jing
    Huang, Shu-ying
    Liu, Gui-Xiang
    Wu, Hui
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2014, 51 (05) : 1293 - 1297
12345