3-allyl-2-(butylsulfanyl)-5,6-dihydrospiro(benzo[h]quinazoline-5,1'-cyclohexane)-4(3H)-one synthesis
- Product Name:3-allyl-2-(butylsulfanyl)-5,6-dihydrospiro(benzo[h]quinazoline-5,1'-cyclohexane)-4(3H)-one
- CAS Number:328070-87-7
- Molecular formula:C24H30N2OS
- Molecular Weight:394.57
![3-prop-2-enyl-2-sulfanylidenespiro[1,6-dihydrobenzo[h]quinazoline-5,1'-cyclohexane]-4-one](/CAS/20210305/GIF/328002-54-6.gif)
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]
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