3,4-Diphenylcinnoline synthesis
- Product Name:3,4-Diphenylcinnoline
- CAS Number:47193-42-0
- Molecular formula:C20H14N2
- Molecular Weight:282.34
Yield:47193-42-0 71%
Reaction Conditions:
with tributyl-amine;tris-(o-tolyl)phosphine;palladium dichloride in N,N-dimethyl-formamide at 90; for 15 h;Inert atmosphere;
Steps:
4.2. General procedure for annulation of 2-iodoaryltriazene with internal alkyne
General procedure: A solution of compound 1 (0.25 mmol), alkyne (0.75 mmol), PdCl2 (3.3 mg, 0.02 mmol), P(o-Tolyl)3 (11.4 mg, 0.04 mmol), and nBu3N (119 μL, 0.50 mmol) in DMF (5 mL) was stirred at 90 °C until 1 was consumed as monitored by TLC. The reaction mixture was allowed to cool to room temperature. The solvent was evaporated and the residue was purified by column chromatography on silica gel (hexane/ethyl acetate/dichloromethane 10-5:1:1) to afford corresponding cinnoline.
References:
Zhu, Chuan;Yamane, Motoki [Tetrahedron,2011,vol. 67,# 26,p. 4933 - 4938] Location in patent:experimental part
