Synthesis, structure and transformations of 2-iminoimidazolidines into novel fused heterocyclic ring systems

被引:3
|
作者
Kornicka, A
Saczewski, F
Gdaniec, M
机构
[1] Med Univ Gdansk, Dept Chem Technol Drugs, PL-80416 Gdansk, Poland
[2] Adam Mickiewicz Univ Poznan, Fac Chem, PL-60780 Poznan, Poland
关键词
imidazolidine; imidazo[2 ',1 ': 4,5][1,3,5]thiadiazino[2,3-b]quinazoline-5-thione; 4H-3,1-benzoxazine; X-ray analysis;
D O I
10.3987/COM-06-10666
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
Reaction of 2-chloro-4,5-dihydroimidazole (1) with 2-aminobenzylamines (2a-d) afforded 2-[(imidazolidin-2-ylideneamino)methyl]anilines (3a-d) which upon treatment with carbon disulfide gave 2,3-dihydro-12H-imidazo[2',1':4,5][1,3,5]thiadiazino[2,3-b]quinazolin-5-thiones (4a-d) and 3,4-dihydro-1H-quinazolin-2-thiones (5a-c). Analogous reaction of 1 with 2-aminobenzyl alcohol (6) led to the formation of [2-(4,5-dihydrol 1H-imidazol-2-ylamino)phenyl]methanol hydrochloride (7) which was transformed into 1-(4H-3,1-benzoxazin-2-yl)imidazolidin-2-thione (8).
引用
收藏
页码:687 / 699
页数:13
相关论文
共 50 条
  • [41] Synthesis of chiral fused heterocyclic compounds containing 1,2,4-triazole ring
    Wang, ZY
    Shi, HX
    Shi, HJ
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2001, 38 (02) : 355 - 357
  • [42] REARRANGEMENTS IN HETEROCYCLIC SYNTHESIS .2. NOVEL TRANSFORMATIONS OF 2-AMINONICOTINONITRILE AND ANTHRANILONITRILE
    HOSMANE, RS
    LIM, BB
    SUMMERS, MF
    SIRIWARDANE, U
    HOSMANE, NS
    CHU, SSC
    JOURNAL OF ORGANIC CHEMISTRY, 1988, 53 (22): : 5309 - 5315
  • [43] Novel Fused Pyrrole Heterocyclic Ring Systems as Structure Analogs of LE 300: Synthesis and Pharmacological Evaluation as Serotonin 5-HT2A, Dopamine and Histamine H1 Receptor Ligands
    Rostom, Sherif A. F.
    ARCHIV DER PHARMAZIE, 2010, 343 (02) : 73 - 80
  • [44] Synthesis, characterization, molecular docking, antimicrobial and antifungal studies of some novel fused-ring heterocyclic compounds
    Vahora, Mohammadishfak Sikandar
    Boruah, Jeena Jyoti
    Lalpara, Jaydeep
    Das, Siva Prasad
    JOURNAL OF CHEMICAL SCIENCES, 2024, 136 (04)
  • [45] ELECTRONIC-STRUCTURE OF CYCLOBUTADIENE FUSED WITH HETEROCYCLIC RING .2. CYCLOBUTADIENES CONDENSED WITH 5-MEMBERED HETEROCYCLIC RINGS
    GHEORGHIU, MD
    FILIP, P
    REVUE ROUMAINE DE CHIMIE, 1976, 21 (08) : 1189 - 1201
  • [46] Synthesis and structure activity relationship of D-homo cyclopamine analogs: A-ring fused heterocyclic analogs
    Grogan, Michael J.
    Lescarbeau, Andre
    Tremblay, Martin R.
    Lin, Grace
    Hagel, Margit
    McGovern, Karen
    Castro, Alfredo C.
    ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2009, 237
  • [47] Multicomponent Synthesis of Novel Penta-Heterocyclic Ring Systems Incorporating a Benzopyranopyridine Scaffold
    Gomha, Sobhi M.
    Riyadh, Sayed M.
    SYNTHESIS-STUTTGART, 2014, 46 (02): : 258 - 262
  • [48] Synthesis of phenanthro[b] phenazine, a novel heterocyclic ring structure for discotic liquid crystals
    Kumar, S
    Manickam, M
    MOLECULAR CRYSTALS AND LIQUID CRYSTALS, 2000, 338 : 175 - +
  • [49] Synthesis and antimicrobial activity of some novel fused heterocyclic moieties
    Seelam, Nareshvarma
    Shrivastava, Satya P.
    Prasanthi, Somarouthu
    ORGANIC COMMUNICATIONS, 2013, 6 (02) : 78 - 85
  • [50] Synthesis of fused heterocyclic systems via the Mallory photoreaction of arylthienylethenes
    Dyachenko, Natalia V.
    Khoroshutin, Andrey V.
    Sotnikova, Yulia A.
    Karnoukhova, Valentina A.
    Tokarev, Sergey D.
    Anisimov, Alexander V.
    Fedorov, Yurii V.
    Fedorova, Olga A.
    PHOTOCHEMICAL & PHOTOBIOLOGICAL SCIENCES, 2019, 18 (12) : 2901 - 2911