Final published version
Licence: CC BY-NC
Research output: Contribution to Journal/Magazine › Journal article › peer-review
Research output: Contribution to Journal/Magazine › Journal article › peer-review
}
TY - JOUR
T1 - A multicomponent reaction of 2-aminoimidazoles
T2 - microwave-assisted synthesis of novel 5-aza-7-deaza-adenines
AU - Lim, Felicia Phei Lin
AU - Low, Szy Teng
AU - Ho, Elvina Lee King
AU - Halcovitch, Nathan R.
AU - Tiekink, Edward R. T.
AU - Dolzhenko, Anton V.
PY - 2017
Y1 - 2017
N2 - An efficient and highly selective multicomponent synthesis of 4-aminoimidazo[1,2-a][1,3,5]triazines, which are 5-aza-7-deaza-isosteres of adenine, was developed. The reaction of 2-aminoimidazoles, triethyl orthoformate and cyanamide under microwave irradiation proceeded regioselectively to provide a library of novel 5-aza-7-deaza-adenines in good yields and purity. The developed method was demonstrated to be scalable and highly reproducible in three different monomode microwave reactors. A rearrangement was proposed to explain the high selectivity of the reaction.
AB - An efficient and highly selective multicomponent synthesis of 4-aminoimidazo[1,2-a][1,3,5]triazines, which are 5-aza-7-deaza-isosteres of adenine, was developed. The reaction of 2-aminoimidazoles, triethyl orthoformate and cyanamide under microwave irradiation proceeded regioselectively to provide a library of novel 5-aza-7-deaza-adenines in good yields and purity. The developed method was demonstrated to be scalable and highly reproducible in three different monomode microwave reactors. A rearrangement was proposed to explain the high selectivity of the reaction.
KW - ADENOSINE RECEPTOR ANTAGONISTS
KW - ONE-POT
KW - SUBSTITUTED 2-AMINO-1H-IMIDAZOLES
KW - PHARMACOLOGICAL-ACTIVITY
KW - BIOLOGICAL EVALUATION
KW - INHIBITORS
KW - DERIVATIVES
KW - PURINOME
KW - ANALOGS
KW - SYSTEM
U2 - 10.1039/c7ra11305f
DO - 10.1039/c7ra11305f
M3 - Journal article
VL - 7
SP - 51062
EP - 51068
JO - RSC Advances
JF - RSC Advances
SN - 2046-2069
IS - 81
ER -