Synthesis of fully substituted pyrazoles from pyridinium 1,4-zwitterionic thiolates and hydrazonoyl chlorides via a [[3 + 3] − 1] pathway-Reference-Cited by-同舟云学术

Synthesis of fully substituted pyrazoles from pyridinium 1,4-zwitterionic thiolates and hydrazonoyl chlorides via a [[3 + 3] − 1] pathway

Published:2020 Issue:15 Volume:18 Page:2949-2955
ISSN:1477-0520
Container-title:Organic & Biomolecular Chemistry
language:en
Short-container-title:Org. Biomol. Chem.

Author:

Cheng Bin¹²³⁴⁵^ORCID,Bao Bian⁵⁶⁷⁸⁴,Xu Wei¹²³⁴⁹,Li Yuntong⁵⁶⁷⁸⁴,Li Hui⁵⁶⁷⁸⁴,Zhang Xinping⁵⁶⁷⁸⁴,Li Yun⁵⁶⁷⁸⁴^ORCID,Wang Taimin¹²³⁴,Zhai Hongbin¹²³⁴⁵^ORCID

Affiliation:

1. Institute of Marine Biomedicine

2. Shenzhen Polytechnic

3. Shenzhen 518055

4. China

5. State Key Laboratory of Applied Organic Chemistry

6. College of Chemistry and Chemical Engineering

7. Lanzhou University

8. Lanzhou 730000

9. Key Laboratory of Wudang Local Chinese Medicine Research and Institute of Medicinal Chemistry

Abstract

Pyrazoles were synthesized from pyridinium 1,4-zwitterionic thiolates and hydrazonoyl chlorides via an unusual [[3 + 3] − 1] pathway, involving a formal [3 + 3] cascade cyclization followed by a spontaneous ring-contraction/sulfur extrusion reaction.

Funder

National Natural Science Foundation of China

Publisher

Royal Society of Chemistry (RSC)

Subject

Organic Chemistry,Physical and Theoretical Chemistry,Biochemistry

Link

http://pubs.rsc.org/en/content/articlepdf/2020/OB/D0OB00224K

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1. Intramolecular Desulfitative Coupling: Nickel-Catalyzed Transformation of Diaryl Sulfones into Biaryls via Extrusion of SO2

2. Domino N2-Extrusion–Cyclization of Alkynylarylketone Derivatives for the Synthesis of Indoloquinolines and Carbocycle-Fused Quinolines

3. A Mild and Efficient CH2-Extrusion Reaction for the Enantiospecific Synthesis of Highly Configurationally Stable Tröger Bases