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 -