One-Pot Parallel Synthesis of Alkyl Sulfides, Sulfoxides, and Sulfones.
A simple and cost-effective one-pot parallel synthesis approach to sulfides, sulfoxides, and sulfones from thiourea was elaborated. The method combines two procedures optimized to the parallel synthesis conditions: alkylation of thiourea with alkyl chlorides and mono or full oxidation of in situ generated sulfides with H2O2 or H2O2-(NH4)2MoO4. The experimental set up required commonly used lab equipment: conventional oven and ultrasonic bath; the work up includes filtration or extraction with chloroform. The method was evaluated on an 81 member library of drug-like sulfides, sulfoxides, and sulfones yielding the compounds on a 30-300 mg scale. A small-scale synthesis of 2-(benzhydrylsulfinyl)acetamide (modafinil) utilizing our approach resulted in similar efficiency to the published procedures.
†Enamine, Ltd., 61 Chervonotkatska Street, Kyiv, 02094, Ukraine.
Andrey V
AV
Bogolubsky
†Enamine, Ltd., 61 Chervonotkatska Street, Kyiv, 02094, Ukraine.|‡ChemBioCenter, Kyiv National Taras Shevchenko University, 61 Chervonotkatska Street, Kyiv, 02094, Ukraine.
Yurii S
YS
Moroz
†Enamine, Ltd., 61 Chervonotkatska Street, Kyiv, 02094, Ukraine.|§Department of Chemistry, Kyiv National Taras Shevchenko University, 64 Volodymyrska Street, Kyiv, 01601, Ukraine.
Pavel K
PK
Mykhailiuk
†Enamine, Ltd., 61 Chervonotkatska Street, Kyiv, 02094, Ukraine.|‡ChemBioCenter, Kyiv National Taras Shevchenko University, 61 Chervonotkatska Street, Kyiv, 02094, Ukraine.
Eugeniy N
EN
Ostapchuk
†Enamine, Ltd., 61 Chervonotkatska Street, Kyiv, 02094, Ukraine.
Alexander V
AV
Rudnichenko
†Enamine, Ltd., 61 Chervonotkatska Street, Kyiv, 02094, Ukraine.
Yurii V
YV
Dmytriv
§Department of Chemistry, Kyiv National Taras Shevchenko University, 64 Volodymyrska Street, Kyiv, 01601, Ukraine.
Anna N
AN
Bondar
§Department of Chemistry, Kyiv National Taras Shevchenko University, 64 Volodymyrska Street, Kyiv, 01601, Ukraine.
Olga A
OA
Zaporozhets
‡ChemBioCenter, Kyiv National Taras Shevchenko University, 61 Chervonotkatska Street, Kyiv, 02094, Ukraine.
Sergey E
SE
Pipko
§Department of Chemistry, Kyiv National Taras Shevchenko University, 64 Volodymyrska Street, Kyiv, 01601, Ukraine.
Roman A
RA
Doroschuk
†Enamine, Ltd., 61 Chervonotkatska Street, Kyiv, 02094, Ukraine.|‡ChemBioCenter, Kyiv National Taras Shevchenko University, 61 Chervonotkatska Street, Kyiv, 02094, Ukraine.
Liudmyla N
LN
Babichenko
†Enamine, Ltd., 61 Chervonotkatska Street, Kyiv, 02094, Ukraine.|∥The Institute of High Technologies, Kyiv National Taras Shevchenko University, 4 Glushkov Street, Building 5, Kyiv, 03187, Ukraine.
Anzhelika I
AI
Konovets
†Enamine, Ltd., 61 Chervonotkatska Street, Kyiv, 02094, Ukraine.|‡ChemBioCenter, Kyiv National Taras Shevchenko University, 61 Chervonotkatska Street, Kyiv, 02094, Ukraine.
Andrey
A
Tolmachev
D000478:Alkylation; D001559:Benzhydryl Compounds / Q000138:chemical synthesis; D002725:Chloroform; D005374:Filtration; D007202:Indicators and Reagents; D000077408:Modafinil; D008982:Molybdenum / Q000737:chemistry; D010084:Oxidation-Reduction; D012997:Solvents; D013440:Sulfides / Q000138:chemical synthesis*; D013450:Sulfones / Q000138:chemical synthesis*; D013454:Sulfoxides / Q000138:chemical synthesis*; D013890:Thiourea / Q000737:chemistry; D014465:Ultrasonics
D001559:Benzhydryl Compounds; D007202:Indicators and Reagents; D012997:Solvents; D013440:Sulfides; D013450:Sulfones; D013454:Sulfoxides; D002725:Chloroform; D008982:Molybdenum; D013890:Thiourea; C022175:ammonium molybdate; D000077408:Modafinil
alkyl chlorides; alkylation of thiourea; ammonium molybdate; one-pot parallel synthesis; oxidation of alkyl sulfides