Shifting Access from Pyrimidine‐Spirofused to Fused Benzoheterocycles by Modifying the Activated Group Position

Author:

Yang Dezhi1,Wang Yan12,Zhang Chun23,Luo Yun1,Zhu Xuecheng2,Zhao Si1,Fu Wenting1,Cheng Bin12ORCID,Zhai Hongbin4,Wang Taimin12

Affiliation:

1. School of Pharmacy Zunyi Medical University Zunyi 563000 People's Republic of China

2. Institute of Marine Biomedicine Shenzhen Polytechnic University Shenzhen 518055 People's Republic of China

3. Key Laboratory of Tropical Medicinal Resource Chemistry of Ministry of Education Hainan Normal University Haikou 571158 People's Republic of China

4. State Key Laboratory of Chemical Oncogenomics Shenzhen Engineering Laboratory of Nano Drug Slow-Release Peking University Shenzhen Graduate School Shenzhen 518055 People's Republic of China

Abstract

AbstractThe synthesis of pyrimidine‐spirofused indolines from 1,3,5‐triazinanes with 2‐sulfonyliminoindolines has been achieved under catalyst‐ and additive‐free conditions, in which five atoms of 1,3,5‐triazinanes were introduced to the spiro‐annulation products via a (5+1) pathway. Subsequently, this strategy was extended to 3‐aminoindoles and 3‐aminobenzothiophenes, but a different reaction pathway (3+3) was observed. In these cases, three‐atoms of 1,3,5‐triazinanes were incorporated into pyrimidine‐fused indoles/benzothiophenes. These two transformations demonstrate the potential and versatility of 1,3,5‐triazinanes to construct nitrogen‐heterocycles.

Funder

National Natural Science Foundation of China

Science, Technology and Innovation Commission of Shenzhen Municipality

Publisher

Wiley

Reference80 articles.

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