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

• Published in: Journal of organic chemistry Vol. 83; no. 3; pp. 1591 - 1597
• Main Authors: Chen, Guihua, Hu, Minglin, Peng, Yungui
• Format: Journal Article
• Language: English
• 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

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...