Access to Fully Substituted Dihydroindazoles Via Hexadehydro-Diels-Alder/[3+2] Cycloaddition

被引:2
|
作者
Xu, Weigang [1 ]
Li, Xiuhuan [2 ]
Zou, Luyao [1 ]
Li, Xiaoli [1 ]
Zhang, Zhiqiang [1 ]
Ali, Sajjad [1 ]
Wang, Zhengshen [1 ]
Li, Pengfei [1 ]
Zheng, Huaiji [1 ]
机构
[1] Northwest Agr & Forestry Univ, Shaanxi Key Lab Nat Prod & Chem Biol, Coll Chem & Pharm, Yangling 712100, Peoples R China
[2] Northwest Agr & Forestry Univ, State Key Lab Crop Stress Biol Arid Areas, Yangling 712100, Peoples R China
来源
JOURNAL OF ORGANIC CHEMISTRY | 2023年 / 88卷 / 20期
基金
中国国家自然科学基金;
关键词
1,3-DIPOLAR CYCLOADDITION; 1H-INDAZOLES; ARYNES; INDAZOLES; CYCLOAROMATIZATION; EFFICIENT; BENZYNES;
D O I
10.1021/acs.joc.3c01901
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A cascade hexadehydro-Diels-Alder (HDDA)/[3 + 2] cycloaddition reaction between tetrayne and N,N '-cyclic acylhydrazone is described. This strategy allows the efficient construction of fully substituted 2,3-dihydro-1H-indazole scaffolds which have insecticidal activity against the third instar larvae of Mythimna separata.
引用
收藏
页码:14736 / 14747
页数:12
相关论文
共 50 条
  • [21] Access to thiazoles via [3+2] cycloaddition of 1,2,3-thiadiazoles with isonitriles
    An, Qiaoyu
    Liu, Lei
    Tang, Zongyuan
    Luo, Han
    Li, You
    Xu, Mingchuan
    Li, Baosheng
    ORGANIC CHEMISTRY FRONTIERS, 2021, 8 (12) : 2909 - 2913
  • [22] Diels-Alder cycloaddition of highly substituted pyran-2-ones with maleic anhydride
    Kranjc, K
    Leban, I
    Polanc, S
    Kocevar, M
    HETEROCYCLES, 2002, 58 : 183 - 190
  • [23] Efficient synthesis of substituted pyrazoles Via [3+2] cycloaddition catalyzed by lipase in ionic liquid
    Li, Fengxi
    Xu, Yaning
    Wang, Ciduo
    Wang, Chunyu
    Xie, Hanqing
    Xu, Yuelin
    Chen, Peng
    Wang, Lei
    PROCESS BIOCHEMISTRY, 2023, 124 : 253 - 258
  • [24] Silver-Catalyzed Asymmetric Desymmetrization of Cyclopentenediones via [3+2] Cycloaddition with α-Substituted Isocyanoacetates
    George, Jimil
    Kim, Hun Young
    Oh, Kyungsoo
    ORGANIC LETTERS, 2018, 20 (08) : 2249 - 2252
  • [25] Intramolecular Diels-Alder and [3+2] Cycloaddition Reactions in the One-Pot Synthesis of Epoxypyrrolo[3,4-g]indazoles
    Alizadeh, Abdolali
    Asalemi, Kaveh Amir Ashjaee
    Halvagar, Mohammadreza
    SYNTHESIS-STUTTGART, 2019, 51 (15): : 2936 - 2944
  • [26] Access to Chromenopyrrole via Tandem [3+2] Cycloaddition and Intramolecular C-O Coupling
    Das, Bubul
    Chakraborty, Nikita
    Dhara, Hirendra Nath
    Bhattacharyya, Pratip
    Patel, Bhisma K.
    JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (02): : 1331 - 1335
  • [27] Dearomatization of Indole via Intramolecular [3+2] Cycloaddition: Access to the Pentacyclic Skeleton of Strychons Alkaloids
    Wang, Zhengshen
    Chen, Luxin
    Yao, Yuan
    Liu, Zhigang
    Gao, Jin-Ming
    She, Xuegong
    Zheng, Huaiji
    ORGANIC LETTERS, 2018, 20 (15) : 4439 - 4443
  • [28] Synthetic Access to Oxazolidin-4-ones via Elimination/[3+2] Cycloaddition Reaction
    Jiang, Shengsheng
    Li, Kai
    Yan, Jun
    Shi, Kuangxi
    Zhao, Chengtao
    Yang, Limin
    Zhong, Guofu
    JOURNAL OF ORGANIC CHEMISTRY, 2017, 82 (18): : 9779 - 9785
  • [29] Access to 4-Oxazolidinones: A (3+2) Cycloaddition Approach
    Acharya, Arjun
    Montes, Karissa
    Jeffrey, Christopher S.
    ORGANIC LETTERS, 2016, 18 (23) : 6082 - 6085
  • [30] Access to Indoles via Diels-Alder Reactions of 3-Vinylpyrroles
    Noland, Wayland E.
    Lanzatella, Nicholas P.
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 2009, 46 (06) : 1285 - 1295