Synthesis of 6-formylsalicylates based on regioselective [3+3] cyclocondensations of 1,3-bis(silyloxy)-1,3-butadienes with 1,1-dichloro-4-ethoxy-3-buten-2-ones

A variety of 6‐(trichloromethyl)salicylates (=2‐hydroxy‐6‐(trichloromethyl)benzoates) were prepared by TiCl4‐mediated cyclization of 1,3‐bis(trimethylsilyloxy)buta‐1,3‐dienes with 1,1,1‐trichloro‐4,4‐dimethoxybut‐3‐en‐2‐one. The employment of trimethylsilyl trifluoromethanesulfonate (Me3SiOTf) as Lewis acid resulted in the formation of trichloromethyl‐substituted cyclohexenones. The cyclizations proceeded with good‐to‐very‐good regioselectivities.

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β-Chloro-α,β-unsaturated carbonyls as convenient precursors of highly substituted benzenes

Barhoumi‐Slimi

Ourévitch

2017

J IRAN CHEM SOC

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Synthesis of 6-formylsalicylates based on regioselective [3+3] cyclocondensations of 1,3-bis(silyloxy)-1,3-butadienes with 1,1-dichloro-4-ethoxy-3-buten-2-ones

Cited by 4 publications

References 33 publications

ChemInform Abstract: Synthesis of 6‐Formylsalicylates (IV), (VII) Based on Regioselective [3 + 3] Cyclocondensations of 1,3‐Bis(silyloxy)‐1,3‐butadienes with 1,1‐Dichloro‐4‐ethoxy‐3‐buten‐2‐ones.

ChemInform Abstract: Synthesis of 6‐Formylsalicylates (IV), (VII) Based on Regioselective [3 + 3] Cyclocondensations of 1,3‐Bis(silyloxy)‐1,3‐butadienes with 1,1‐Dichloro‐4‐ethoxy‐3‐buten‐2‐ones.

Regioselective Synthesis of Trichloromethyl‐Substituted Salicylates and Cyclohexenones by One‐Pot Cyclizations of 1,3‐Bis(trimethylsilyloxy)buta‐1,3‐dienes

β-Chloro-α,β-unsaturated carbonyls as convenient precursors of highly substituted benzenes

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