Preparation of 8-(arylsulfanyl)adenines with diazonium salts under mild, aerobic conditions.
8-(Arylsulfanyl)adenines 11 were prepared in up to 75% yield by reacting the 8-thionoadenine 6 (acetic acid 3-(6-amino-8-thioxo-7,8-dihydropurin-9-yl)propyl ester) with benzenediazonium tetrafluoroborates in DMSO. Benzenediazonium ions carrying an electron-withdrawing substituent gave the highest yields. The reaction proceeded smoothly at room temperature without any base and could be performed under air atmosphere. The extremely mild conditions are compatible with a wide range of functional groups.
Biamonte
Marco A
MA
Conforma Therapeutics Corporation, 9393 Towne Centre Drive, Suite 240, San Diego, California 92121, USA. mbiamonte@conformacorp.com
Shi
Jiandong
J
Hurst
David
D
Hong
Kevin
K
Boehm
Marcus F
MF
Kasibhatla
Srinivas R
SR
D000225:Adenine / Q000031:analogs & derivatives* / Q000737:chemistry / Q000494:pharmacology; D002851:Chromatography, High Pressure Liquid; D003979:Diazonium Compounds / Q000737:chemistry*; D018841:HSP90 Heat-Shock Proteins / Q000037:antagonists & inhibitors; D015394:Molecular Structure; D010100:Oxygen / Q000737:chemistry*; D012997:Solvents
D003979:Diazonium Compounds; D018841:HSP90 Heat-Shock Proteins; D012997:Solvents; C035176:benzenediazonium; D000225:Adenine; D010100:Oxygen