Switchable Synthesis of 3‑Substituted 1H‑Indazoles and 3,3-Disubstituted 3H‑Indazole-3-phosphonates Tuned by Phosphoryl Groups

3-Alkyl/aryl-1H-indazoles and 3-alkyl/aryl-3H-indazole-3-phosphonates were synthesized efficiently through a 1,3-dipolar cycloaddition reaction between α-substituted α-diazomethylphosphonates and arynes under simple reaction conditions. The product distribution was controlled by the phosphoryl group...

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Bibliographic Details
Published inJournal of organic chemistry Vol. 83; no. 3; pp. 1591 - 1597
Main Authors Chen, Guihua, Hu, Minglin, Peng, Yungui
Format Journal Article
LanguageEnglish
Published WASHINGTON American Chemical Society 02.02.2018
Amer Chemical Soc
Subjects
Chemistry
Chemistry, Organic
cycloaddition reactions
moieties
organic chemistry
organic compounds
Physical Sciences
Science & Technology
ASYMMETRIC MANNICH REACTION
1,3-DIPOLAR CYCLOADDITIONS
PHOSPHONATES
DIELS-ALDER REACTIONS
REGIOSELECTIVE SYNTHESIS
INDAZOLES
DIAZO-COMPOUNDS
ALPHA-DIAZOMETHYLPHOSPHONATES
ARYNES
BOND
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Summary:3-Alkyl/aryl-1H-indazoles and 3-alkyl/aryl-3H-indazole-3-phosphonates were synthesized efficiently through a 1,3-dipolar cycloaddition reaction between α-substituted α-diazomethylphosphonates and arynes under simple reaction conditions. The product distribution was controlled by the phosphoryl group, which acted both as a tuning group and a traceless group in the reaction.
Bibliography:ObjectType-Article-1
SourceType-Scholarly Journals-1
ObjectType-Feature-2
content type line 23
ISSN:0022-3263
1520-6904
1520-6904
DOI:10.1021/acs.joc.7b02857