Reaction of Phosphines with 1-Azido-(2-halogenomethyl)benzene Giving Aminophosphonium-Substituted Indazoles | Zendy

Thibault Tannoux | Zendy; Nicolas Casaretto | Zendy; Sophie Bourcier | Zendy; Vincent Gandon | Zendy; Audrey Auffrant | Zendy

AI Assistant Blog Pricing

Home ZAIA Blog

Open Access

Reaction of Phosphines with 1-Azido-(2-halogenomethyl)benzene Giving Aminophosphonium-Substituted Indazoles

Author(s) -

Thibault Tannoux,

Nicolas Casaretto,

Sophie Bourcier,

Vincent Gandon,

Audrey Auffrant

Publication year - 2020

Publication title -

the journal of organic chemistry

Language(s) - English

Resource type - Journals

SCImago Journal Rank - 1.2

H-Index - 228

eISSN - 1520-6904

pISSN - 0022-3263

DOI - 10.1021/acs.joc.0c02371

Subject(s) - chemistry , phosphine , reagent , adduct , phosphonium , acetonitrile , bicyclic molecule , toluene , indazole , benzene , halogen , medicinal chemistry , triphenylphosphine , tributylphosphine , solvent , organic chemistry , catalysis , alkyl

The reaction between a 1-azido-(2-halogenomethyl)benzene and a phosphine gives different products depending on the nature of the halogen, the phosphine itself, and the solvent employed. While PPh 3 (2 equiv) reacts with the chloro reagent in toluene to give the expected iminophosphorane-phosphonium adduct, trialkylphosphines (PCy 3 and PE 3 ) surprisingly furnish an aminophosphonium substituted by a zwitterionic indazole. The bicyclic product can also form from PPh 3 using the bromo reagent in acetonitrile. A mechanism is proposed for this cyclization based on DFT calculations.

The content you want is available to Zendy users.

Already have an account? Click here to sign in.

Having issues? You can contact us here

Accelerating Research