New Cyano-Group-Containing 1,3-Oxaselenoles: Nucleophilic Substitution of a Cyano Group with Rearrangement

被引：1
|
作者：
Kachanov, Andrey V. [1 ]
Zamaraev, Andrey V. [2 ]
Gerasimenko, Andrey V. [3 ]
Maslov, Konstantin V. [1 ]
Slabko, Oleg Yu. [1 ]
Kaminskii, Vladimir A. [1 ]
机构：
[1] Far Eastern Fed Univ, Sch Nat Sci, Sukhanov Str 8, Vladivostok 690950, Russia
[2] Russian Acad Sci, Far East Branch, GB Elyakov Pacific Inst Bioorgan Chem, Prospect 100 Let Vladivostoku 159, Vladivostok 690022, Russia
[3] Russian Acad Sci, Far East Branch, Inst Chem, Prospect 100 Let Vladivostoku 159, Vladivostok 690022, Russia
来源：
SYNLETT | 2018年 / 29卷 / 15期
关键词：
aroylacetonitriles; selenium oxide; oxaselenoles; nucleophilic substitution; rearrangement; SELENIUM DIOXIDE; MALONONITRILE; DERIVATIVES; OXIDATION; YLIDES; ROUTE;
D O I：
10.1055/s-0037-1609939
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
New cyano-group-containing 1,3-oxaselenoles were obtained by the treatment of aroylacetonitriles with selenium(IV) oxide. The resulting products were shown to react with ammonia, hydrazine, or primary amines; this reaction was accompanied by aryl rearrangement.
引用
收藏
页码：2035 / 2038
页数：4
相关论文
共 50 条
  • [41] Computational and experimental investigations of a cyano group containing novel small molecule organic semiconductor
    C. Yorur Goreci
    M. Kazici
    S. Bozar
    H. Gokce
    S. Gunes
    Journal of Materials Science: Materials in Electronics, 2021, 32 : 14749 - 14763
  • [42] A new leaving group in nucleophilic aromatic substitution reactions (SNAr)
    Bakavoli, Mehdi
    Pordel, Mehdi
    Rahimizadeh, Mohammad
    Jahandari, Pooneh
    JOURNAL OF CHEMICAL RESEARCH, 2008, (08) : 432 - 433
  • [43] Stability of Trithiocarbonate RAFT Agents Containing Both a Cyano and a Carboxylic Acid Functional Group
    Fuchs, Adrian V.
    Thurecht, Kristofer J.
    ACS MACRO LETTERS, 2017, 6 (03): : 287 - 291
  • [44] Computational and experimental investigations of a cyano group containing novel small molecule organic semiconductor
    Goreci, C. Yorur
    Kazici, M.
    Bozar, S.
    Gokce, H.
    Gunes, S.
    JOURNAL OF MATERIALS SCIENCE-MATERIALS IN ELECTRONICS, 2021, 32 (11) : 14749 - 14763
  • [45] Synthesis and Dimroth rearrangement of 6-cyano-1,2,4-triazolo[4,3-a]pyrimidin-5- and 7-ones.: A novel alkylation with orthoesters and a new participation of the cyano group in the rearrangement
    El Ashry, ESH
    El Kilany, Y
    Rashed, N
    Mousaad, A
    Assafir, H
    ZEITSCHRIFT FUR NATURFORSCHUNG SECTION B-A JOURNAL OF CHEMICAL SCIENCES, 1998, 53 (10): : 1203 - 1212
  • [46] A NEW TYPE OF INTRAMOLECULAR GROUP-TRANSFER IN STEROID PHOTOCHEMISTRY - A CONTRIBUTION TO MECHANISM OF OXIDATIVE CYANOHYDRIN-CYANO-KETONE REARRANGEMENT
    KALVODA, J
    JOURNAL OF THE CHEMICAL SOCIETY D-CHEMICAL COMMUNICATIONS, 1970, (16): : 1002 - &
  • [47] ACTIVATION BY A CYANO GROUP .2. NEW SYNTHESIS OF SUBSTITUTED PRIMARY ALCOHOLS
    DEBAL, A
    CUVIGNY, T
    LARCHEVEQUE, M
    SYNTHESIS-STUTTGART, 1976, (06): : 391 - 393
  • [48] HOMOLYTIC REARRANGEMENT WITH MIGRATION OF A HYDROGEN-ATOM AND A CYANO GROUP DURING THE OXIDATION OF ALPHA-CYANOALKANOLS
    NIKISHIN, GI
    TROYANSKII, EI
    VELIBEKOVA, DS
    OGIBIN, YN
    BULLETIN OF THE ACADEMY OF SCIENCES OF THE USSR DIVISION OF CHEMICAL SCIENCE, 1978, 27 (10): : 2166 - 2166
  • [49] Development of phenazine-2,3-diol-based photosensitizers: effect of substitution of the cyano group for the nitro group on singlet oxygen generation
    Ohira, Kazuki
    Yu, Chih-Hsin
    Imato, Keiichi
    Ooyama, Yousuke
    NEW JOURNAL OF CHEMISTRY, 2023, 47 (36) : 16799 - 16808
  • [50] Substitution effects of cyano group on the electropolymerization, thermal stability, morphology, and supercapacitor performance of indole based polymers
    Zhu, Danhua
    Zhu, Zhengyou
    Ma, Xiumei
    Xu, Jingkun
    Zhou, Weiqiang
    SYNTHETIC METALS, 2023, 297
12345