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Chinese Journal of Organic Chemistry >

2024 , Vol. 44 >Issue 7: 2223 - 2232

DOI: https://doi.org/10.6023/cjoc202403012

ARTICLES

Synthesis of Spiropyrans via Rh(III)-Catalyzed [3+3] Cyclization of 3-Aryl-2H-1,4-benzoxazine and Diazonaphthalene-2H-ones

  • Mengke Wen ,
  • Yiyue Li ,
  • Haokang Du ,
  • Zhangpei Chen ,
  • Xifa Yang
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  • a Department of Chemistry, College of Sciences, Northeastern University, Shenyang, Liaoning 110819
    b Department of Pesticide Science, College of Plant Protection, Henan Agricultural University, Zhengzhou, Henan 450002
* E-mail: ;

Received date: 2024-03-10

  Revised date: 2024-04-02

  Online published: 2024-04-25

Supported by

National Natural Science Foundation of China(22201066); Science and Technology Planning Project of Henan Province(222102110259)

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Abstract

Rh(III)-catalyzed 1∶1 coupling of 3-aryl-2H-benzo[b][1,4]oxazines with diazonaphthalene-2H-ones has been realized for mild synthesis of NH-containing spiropyrans. The reaction proceeded via C—H activation followed [3+3] annulation with decent functional group tolerance. Preliminary mechanistic studies have been conducted and a plausible mechanism has been proposed.

Key words： spiropyrans; Rh(III); C—H activation; benzoxazines; diazonaphthalen-2H-ones

Cite this article

Mengke Wen , Yiyue Li , Haokang Du , Zhangpei Chen , Xifa Yang . Synthesis of Spiropyrans via Rh(III)-Catalyzed [3+3] Cyclization of 3-Aryl-2H-1,4-benzoxazine and Diazonaphthalene-2H-ones[J]. Chinese Journal of Organic Chemistry, 2024 , 44(7) : 2223 -2232 . DOI: 10.6023/cjoc202403012

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