Iodine mediated nitrosation of imidazo[1,5-a]N-heteroarenes using TBN (tBuONO) reagent

被引：0
|
作者：
Sandeep, Mummadi [1 ,2 ]
Muzaffar-ur-Rehman, Md [1 ]
Chahal, Kapil [1 ,2 ]
Reddy, Kallu Rajender [1 ,2 ]
机构：
[1] CSIR Indian Inst Chem Technol, Catalysis & Fine Chem Div, Hyderabad 500007, India
[2] Acad Sci & Innovat Res AcSIR, Ghaziabad 201002, UP, India
来源：
TETRAHEDRON LETTERS | 2021年 / 82卷
关键词：
Nitrosation; TBN; Iodine; Imidazo[1; 5-a]N-heteroarenes; TERT-BUTYL NITRITE; ONE-POT SYNTHESIS; C-H; ENANTIOSELECTIVE SYNTHESIS; ARYL FORMAMIDES; FACILE ACCESS; METAL; NITROSOARENES; RADICALS; AMINES;
D O I：
10.1016/j.tetlet.2021.153401
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
An iodine mediated regio-selective nitrosation of imidazo[1,5-a]N-heteroarenes is reported using TBN as nitroso source. This method afford synthetically useful and medicinally interesting 3-nitroso imidazo [1,5-a]N-heteroarenes in moderate to good yields with good functional group tolerance. Further, this reaction could applicable on gram-scale level synthesis. (C) 2021 Elsevier Ltd. All rights reserved.
引用
收藏
页数：6
相关论文
共 50 条
  • [41] Synthesis of Cyanide-Functionalized Imidazo[1,5-a]quinolines via Copper-Mediated Aerobic Three-Component Cyclizations
    Feng, Cheng-Tao
    Wei, Hong-Juan
    Li, Jing
    Peng, Ya
    Xu, Kun
    ADVANCED SYNTHESIS & CATALYSIS, 2018, 360 (24) : 4726 - 4730
  • [42] Synthesis of imidazo[1,5-a]pyridines via I2-mediated sp3 C-H amination
    Hu, Zhiyuan
    Hou, Jiao
    Liu, Jie
    Yu, Wenquan
    Chang, Junbiao
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2018, 16 (31) : 5653 - 5660
  • [43] IMINOPHOSPHORANE-MEDIATED ANNELATION OF AN IMIDAZOLE RING INTO A BENZIMIDAZOLE RING - SYNTHESIS OF IMIDAZO[1,5-A]BENZIMIDAZOLE DERIVATIVES - CRYSTAL-STRUCTURE OF 1-(4-METHOXYPHENYLIMINO)-2-(4-METHOXYPHENYLCARBAMOYL)-2,3-DIHYDRO-1H-IMIDAZO[1,5-A]BENZIMIDAZOLE
    MOLINA, P
    ALAJARIN, M
    LOPEZLEONARDO, C
    MADRID, I
    FOCESFOCES, C
    CANO, FH
    TETRAHEDRON, 1989, 45 (06) : 1823 - 1832
  • [44] Mg3N2-assisted one-pot synthesis of 1,3-disubstituted imidazo[1,5-a]pyridine
    Patil, Suhas G.
    Jadhav, Jagannath S.
    Sankpal, Sagar T.
    RSC ADVANCES, 2020, 10 (20) : 11808 - 11815
  • [45] Divalent metal complexes of N,O- and N,N-bidentate imidazo[1,5-a] pyridine ligands: Synthesis, crystal structures, and photophysical properties
    Imada, Yasushi
    Mukai, Shoma
    Tahara, Koki
    Kozai, Natsumi
    Itaya, Masami
    Yoshida, Yasushi
    Ueta, Shoko
    Arakawa, Yukihiro
    Minagawa, Keiji
    Yagishita, Fumitoshi
    INORGANICA CHIMICA ACTA, 2023, 555
  • [46] Imidazo[1,5-a]pyridin-3-ylidenes as π-accepting carbene ligands: substituent effects on properties of N-heterocyclic carbenes
    Koto, Yuma
    Shibahara, Fumitoshi
    Murai, Toshiaki
    ORGANIC & BIOMOLECULAR CHEMISTRY, 2017, 15 (08) : 1810 - 1820
  • [47] CBr4 Mediated [4+1] Dehydrocyclization for the Synthesis of Functionalized Imidazo[1,5-a]heterocycles from Pyridin-2-ylmethanamines and Aldehydes
    Wang, Qiang
    Zha, Meng
    Zhou, Feilong
    Chen, Xixi
    Wang, Baiyu
    Liu, Guodong
    Qian, Lisheng
    ACS OMEGA, 2021, 6 (31): : 20303 - 20308
  • [48] T3P-Mediated N-N Cyclization for the Synthesis of 1,2,4-Triazolo[1,5-a]pyridines
    Ayothiraman, Rajaram
    Bandaru, Durgarao
    Paranthaman, Ranjitha
    Fenster, Michael
    Eastgate, Martin D.
    Vaidyanathan, Rajappa
    ORGANIC PROCESS RESEARCH & DEVELOPMENT, 2019, 23 (11) : 2510 - 2515
  • [49] N,N-DIETHYLCARBOXAMIDES OF IMIDAZO-[1,2-A]-PYRIDINE, S-TRIAZOLO-[4,3-A] AND [1,5-A]-PYRIDINE, AND RELATED RING-SYSTEMS
    CASAGRANDE, C
    INVERNIZZI, A
    FARMACO-EDIZIONE SCIENTIFICA, 1972, 27 (02): : 101 - +
  • [50] A new and efficient synthesis of imidazo[1,5-a]pyridine derivatives by a tandem aza-Wittig/electrocyclic ring closure of N-vinylic phosphazenes
    Palacios, F.
    Alonso, C.
    Rublales, G.
    Textile Dyer and Printer, 1994, 27 (17):
12345