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Synthesis 2021; 53(19): 3578-3584
DOI: 10.1055/a-1509-5175
paper

Synthesis of Spiro[indazole-3,3′-indolin]-2′-ones and Indazolo [2,3-c]quinazolin-6(5H)-ones from Arynes and Isatin-Derived N-Tosylhydrazones

Bin Cheng∗
a   Institute of Marine Biomedicine/Hoffmann Institute of Advanced Materials, Shenzhen Polytechnic, Shenzhen 518055, P. R. of China
b   State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, P. R. of China
,
Yixuan He
a   Institute of Marine Biomedicine/Hoffmann Institute of Advanced Materials, Shenzhen Polytechnic, Shenzhen 518055, P. R. of China
b   State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, P. R. of China
,
Xinping Zhang
a   Institute of Marine Biomedicine/Hoffmann Institute of Advanced Materials, Shenzhen Polytechnic, Shenzhen 518055, P. R. of China
b   State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, P. R. of China
,
Hui Li
a   Institute of Marine Biomedicine/Hoffmann Institute of Advanced Materials, Shenzhen Polytechnic, Shenzhen 518055, P. R. of China
b   State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, P. R. of China
,
Zijie Ding
b   State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, P. R. of China
,
Lizhe Feng
b   State Key Laboratory of Applied Organic Chemistry, College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou 730000, P. R. of China
,
Haiyan Sun
a   Institute of Marine Biomedicine/Hoffmann Institute of Advanced Materials, Shenzhen Polytechnic, Shenzhen 518055, P. R. of China
,
Taimin Wang∗
a   Institute of Marine Biomedicine/Hoffmann Institute of Advanced Materials, Shenzhen Polytechnic, Shenzhen 518055, P. R. of China
,
Hongbin Zhai∗
a   Institute of Marine Biomedicine/Hoffmann Institute of Advanced Materials, Shenzhen Polytechnic, Shenzhen 518055, P. R. of China
c   State Key Laboratory of Chemical Oncogenomics, Shenzhen Engineering Laboratory of Nano Drug Slow-Release, Peking University Shenzhen Graduate School, Shenzhen 518055, P. R. of China
› Author AffiliationsWe thank the National Natural Science Foundation of China (NSFC; Nos. 21971092, 21901014, 21472072, 21871018, 21732001, and 21672017), the Program for Changjiang Scholars and Innovative Research Team in University (No. PCSIRT: IRT_15R28), the Characteristic Innovation Project of Guangdong Provincial Education Department (No. 2020KTSCX295), and the Shenzhen Science and Technology Innovation Committee (No. JCYJ20170818114529521) for financial support.
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Abstract

A formal (3+2) annulation reaction between isatin-derived N-tosylhydrazones and o-(trimethylsilyl)aryl triflates allows facile synthesis of spiro[indazole-3,3′-indolin]-2′-ones in high to excellent yields. Furthermore, indazolo[2,3-c]quinazolin-6(5H)-ones could be accessed from the same starting materials in one-pot fashion via an annulation/rearrangement pathway.

Key words

arynes - isatin - N-tosylhydrazone - formal (3+2) annulations - isomerization - spiro compounds

Supporting Information

    Supporting information for this article is available online at https://doi.org/10.1055/a-1509-5175.
  • Supporting Information


Publication History

Received: 12 April 2021

Accepted after revision: 17 May 2021

Accepted Manuscript online:
17 May 2021

Article published online:
15 June 2021

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