Thermal induced intramolecular [2+2] cycloaddition of allene-ACPs

被引：32
|
作者：
Chen, Kai [1 ,2 ]
Sun, Run [1 ,2 ]
Xu, Qin [1 ,2 ]
Wei, Yin [3 ]
Shi, Min [1 ,2 ,3 ]
机构：
[1] E China Univ Sci & Technol, Key Lab Adv Mat, Shanghai 200237, Peoples R China
[2] E China Univ Sci & Technol, Inst Fine Chem, Shanghai 200237, Peoples R China
[3] Chinese Acad Sci, Shanghai Inst Organ Chem, State Key Lab Organometall Chem, Shanghai 200032, Peoples R China
来源：
ORGANIC & BIOMOLECULAR CHEMISTRY | 2013年 / 11卷 / 24期
基金：
中国国家自然科学基金;
关键词：
UNIQUE TETRASUBSTITUTED ALKENE; MGI2-MEDIATED RING EXPANSIONS; ACID-MEDIATED CYCLOADDITION; TETHERED ALKYLIDENECYCLOPROPANES; CYCLOBUTANE DERIVATIVES; PYRROLIDINE SKELETONS; BOND-CLEAVAGE; METHYLENECYCLOPROPANES; EFFICIENT; LEWIS;
D O I：
10.1039/c3ob40911b
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
A facile synthetic method for preparation of bicyclo[4.2.0] nitrogen heterocycles has been developed via a thermal induced intramolecular [2 + 2] cycloaddition reaction of allene-ACPs. The DFT calculations indicate that this intramolecular cycloaddition proceeds in a concerted manner and a strained small ring is essential.
引用
收藏
页码：3949 / 3953
页数：5
相关论文
共 50 条
  • [41] ELECTRON-TRANSFER-INDUCED INTRAMOLECULAR [2+2] CYCLOADDITION OF 2,6-DIARYLHEPTA-1,6-DIENES
    TAKAHASHI, Y
    OKITSU, O
    ANDO, M
    MIYASHI, T
    TETRAHEDRON LETTERS, 1994, 35 (23) : 3953 - 3956
  • [42] Thermal-Induced Synthesis of Cyclobute[b]indolines via Intramolecular Formal [2+2] Cycloaddition of Enamines and Triazole-derived Ketenimines
    Luo, Huan
    Wang, Han
    Zhang, Wenzheng
    Xu, Ze-Feng
    Duan, Shengguo
    Li, Chuan-Ying
    ADVANCED SYNTHESIS & CATALYSIS, 2024, 366 (18) : 3790 - 3795
  • [43] ON THE MECHANISM OF THERMAL 2+2 CYCLOADDITION REACTIONS INVOLVING FLUOROOLEFINS
    ROBERTS, DW
    TETRAHEDRON, 1985, 41 (23) : 5529 - 5542
  • [44] SYNTHESIS OF HETEROCYCLES BY THERMAL (2+2)-CYCLOADDITION REACTIONS OF ACETYLENES
    REINHOUDT, DN
    BULLETIN DES SOCIETES CHIMIQUES BELGES, 1981, 90 (06): : 633 - 643
  • [45] Strain-Release Promoted Thermal [2+2] Cycloaddition and Photochemical [2+2] Cycloreversion of a Tetraorganylaminoborane
    Keck, Constanze
    Maichle-Moessmer, Caecilia
    Bettinger, Holger F.
    ORGANOMETALLICS, 2023, 42 (16) : 2269 - 2276
  • [46] 3,4-homoadamantadiene: Generation and regioselective [2+2] cycloaddition of a novel tricyclic bridgehead allene
    Ogawa, K
    Okazaki, T
    Kinoshita, T
    JOURNAL OF ORGANIC CHEMISTRY, 2003, 68 (04): : 1579 - 1581
  • [47] Stereocontrolled entry to the tricyclo[3.3.0]oxoheptane core of bielschowskysin by a [2+2] cycloaddition of an allene-butenolide
    Miao, Ru
    Gramani, Subramanian G.
    Lear, Martin J.
    TETRAHEDRON LETTERS, 2009, 50 (15) : 1731 - 1733
  • [48] Intramolecular [2+2] and [4+2] Cycloaddition Reactions of Cinnamylamides of Ethenetricarboxylate in Sequential Processes
    Yamazaki, Shoko
    Sugiura, Hirotaka
    Ohashi, Shinnosuke
    Ishizuka, Keisuke
    Saimu, Rina
    Mikata, Yuji
    Ogawa, Akiya
    JOURNAL OF ORGANIC CHEMISTRY, 2016, 81 (22): : 10863 - 10886
  • [49] Sequential oxidation/thermal induced intramolecular [2+2] cycloaddition of propynol-vinylidenecyclopropanes: access to novel cyclobutene-containing spiro[2.3]hexenes
    Yang, Song
    Xu, Qin
    Shi, Min
    TETRAHEDRON, 2016, 72 (05) : 584 - 591
  • [50] Reagent-Controlled Regioselective Intramolecular [2+2] Cycloaddition between Vinylsilanes and Allenes
    Yoshioka, Shohei
    Takehara, Tsunayoshi
    Suzuki, Takeyuki
    Arisawa, Mitsuhiro
    CHEMISTRY-A EUROPEAN JOURNAL, 2023, 29 (17)
12345