3-allyl-2-(butylsulfanyl)-5,6-dihydrospiro(benzo[h]quinazoline-5,1'-cyclohexane)-4(3H)-one synthesis

Yield:328070-87-7 74%

Reaction Conditions:

with caesium carbonate in butanone at 70; for 16 h;Inert atmosphere;

Steps:

5.2.4 General Method A for generating compounds 1, 6a-e

General procedure: Compound 5 (100 mg, 0.295 mmol) was combined with base (0.443 mmol) and alkylating agent (0.325 mmol) in ethanol or MEK (1.75 mL). The suspension was warmed to 70 °C and allowed to stir for 16 h. The suspension was subsequently diluted with EtOAc and washed with water and brine. The isolated organic layer was then dried over MgSO₄, filtered, and concentrated in vacuo. Further purification via flash chromatography (0% to 10% EtOAc/hex) delivered the desired compounds in 72-83% yield.

References:

Yestrepsky, Bryan D.;Xu, Yuanxi;Breen, Meghan E.;Li, Xiaoqin;Rajeswaran, Walajapet G.;Ryu, Jenny G.;Sorenson, Roderick J.;Tsume, Yasuhiro;Wilson, Michael W.;Zhang, Wenpeng;Sun, Duxin;Sun, Hongmin;Larsen, Scott D. [Bioorganic and Medicinal Chemistry,2013,vol. 21,# 7,p. 1880 - 1897]