Microwave assisted, sequential two-step, one-pot synthesis of novel imidazo[1,2-a] pyrimidine containing tri/tetrasubstituted imidazole derivatives

A series of novel imidazo[1,2-a]pyrimidine containing tri/tetrasubstituted imidazole derivatives (1-10) has been synthesized via sequential two-step, one-pot, multicomponent reaction using imidazo[1,2-a]pyrimidine-2-carbaldehyde, benzil, primary amines, and ammonium acetate catalyzed by p-toluenesulfonic acid under microwave-assisted conditions. The results showed that target compounds can be obtained from a wide range of primary amines bearing different functional groups with moderate to good yields (46%-80%) under optimum reaction conditions. This method provides a green protocol for imidazo[1,2-a]pyrimidine containing tri/tetrasubstituted imidazole derivatives due to ethyl alcohol as a green solvent, microwave irradiation as a greener heating method and one-pot multicomponent reaction as a green technique. The synthesized compounds have been elucidated using various spectroscopic tools such as FT-IR, H-1 NMR, C-13 NMR, and MS.

Keywords:

Imidazo[1, 2-a]pyrimidine, tri/tetrasubstituted imidazole, microwave synthesis, sequential, one-pot reaction p-toluenesulfonic acid,

PDF

___

ABRAHAMS SL, 1989, J PHARMACOL EXP THER, V249, P359
Aeluri R, 2015, EUR J MED CHEM, V100, P18, DOI 10.1016/j.ejmech.2015.05.037
Arafa WAA, 2018, RSC ADV, V8, P16392, DOI 10.1039/c8ra02755b
Bahrami K, 2011, MONATSH CHEM, V142, P159, DOI 10.1007/s00706-010-0428-8
Bhaskaruni SVHS, 2020, ARAB J CHEM, V13, P1142, DOI 10.1016/j.arabjc.2017.09.016
CLEMENTSJEWERY S, 1988, J MED CHEM, V31, P1220, DOI 10.1021/jm00401a025
Esmaeilpour M, 2015, NEW J CHEM, V39, P3388, DOI 10.1039/c5nj00050e
Fang Y, 2017, RES CHEM INTERMEDIAT, V43, P4413, DOI 10.1007/s11164-017-2886-7
FEELY M, 1989, EUR J PHARMACOL, V164, P377, DOI 10.1016/0014-2999(89)90482-2
GEDYE R, 1986, TETRAHEDRON LETT, V27, P279, DOI 10.1016/S0040-4039(00)83996-9
Ghorbani-Vaghei R, 2018, MONATSH CHEM, V149, P1447, DOI 10.1007/s00706-018-2167-1
GIGUERE RJ, 1986, TETRAHEDRON LETT, V27, P4945, DOI 10.1016/S0040-4039(00)85103-5
Goel R, 2015, RSC ADV, V5, P81608, DOI 10.1039/c5ra14795f
Green MD, 2009, POLYM REV, V49, P291, DOI 10.1080/15583720903288914
Gungor T, 2020, BALIKESIR UNIV BILIM, V22, P428, DOI [10.25092/baunfbed.707673, DOI 10.25092/baunfbed.707673]
Gungor T, 2020, MONATSH CHEM, V151, P781, DOI 10.1007/s00706-020-02601-w
Heravi MM, 2008, MONATSH CHEM, V139, P31, DOI 10.1007/s00706-007-0736-9
Kappe CO, 2009, MOL DIVERS, V13, P71, DOI 10.1007/s11030-009-9138-8
Karimi-Jaberi Z, 2010, CHINESE CHEM LETT, V21, P1183, DOI 10.1016/j.cclet.2010.06.012
Khalafi-Nezhad A, 2016, RSC ADV, V6, P67281, DOI 10.1039/c6ra11171h
Kumar BRP, 2009, J HETEROCYCLIC CHEM, V46, P278, DOI 10.1002/jhet.68
Kumar D, 2012, GREEN CHEM, V14, P2038, DOI 10.1039/c2gc35277j
Kurumurthy C, 2012, RES CHEM INTERMEDIAT, V38, P359, DOI 10.1007/s11164-011-0352-5
Lidstrom P, 2001, TETRAHEDRON, V57, P9225, DOI 10.1016/S0040-4020(01)00906-1
Higuera NL, 2019, SYNLETT, V30, P225, DOI 10.1055/s-0037-1610679
Mader M, 2008, BIOORG MED CHEM LETT, V18, P179, DOI 10.1016/j.bmcl.2007.10.106
Mantipally M, 2019, BIOORG MED CHEM LETT, V29, P2248, DOI 10.1016/j.bmcl.2019.06.031
MOOG C, 1994, ANTIVIR RES, V24, P275, DOI 10.1016/0166-3542(94)90075-2
Moosavi-Zare AR, 2014, RSC ADV, V4, P60636, DOI 10.1039/c4ra10589c
Moseley JD, 2011, GREEN CHEM, V13, P794, DOI 10.1039/c0gc00823k
Nejatianfar M, 2018, APPL ORGANOMET CHEM, V32, DOI 10.1002/aoc.4095
Rossi R, 2019, ADV SYNTH CATAL, V361, P2737, DOI 10.1002/adsc.201801381
Rupert KC, 2003, BIOORG MED CHEM LETT, V13, P347, DOI 10.1016/S0960-894X(02)01020-X
Shaikh M, 2020, POLYCYCL AROMAT COMP, V40, P1315, DOI 10.1080/10406638.2018.1544154
Sharma GVM, 2014, MEDCHEMCOMM, V5, P1751, DOI 10.1039/c4md00277f
Shoar RH, 2010, SYNTHETIC COMMUN, V40, P1270, DOI 10.1080/00397910903068204
Singh H, 2018, APPL ORGANOMET CHEM, V32, DOI 10.1002/aoc.3989
SPITZER WA, 1988, J MED CHEM, V31, P1590, DOI 10.1021/jm00403a018
Taha NI, 2018, INT J ORGANIC CHEM, V8, P309, DOI [10.4236/ ijoc.2018.83023, DOI 10.4236/IJOC.2018.83023]
Takle AK, 2006, BIOORG MED CHEM LETT, V16, P378, DOI 10.1016/j.bmcl.2005.09.072
Nguyen TB, 2018, EUR J ORG CHEM, V2018, P5861, DOI 10.1002/ejoc.201800458
TULLY WR, 1991, J MED CHEM, V34, P2060, DOI 10.1021/jm00111a021
Verma P, 2020, J MOL STRUCT, V1203, DOI 10.1016/j.molstruc.2019.127410
Vitaku E, 2014, J MED CHEM, V57, P10257, DOI 10.1021/jm501100b
Wang LM, 2006, J FLUORINE CHEM, V127, P1570, DOI 10.1016/j.jfluchem.2006.08.005
Wolkenberg SE, 2004, ORG LETT, V6, P1453, DOI 10.1021/ol049682b
Wu L, 2012, J CHIL CHEM SOC, V57, P1204, DOI 10.4067/S0717-97072012000300002
Xu F, 2013, J HETEROCYCLIC CHEM, V50, P668, DOI 10.1002/jhet.1818
Zhou JF, 2005, SYNTHETIC COMMUN, V35, P1369, DOI 10.1081/SCC-200057281
Zhou JP, 2008, CHINESE CHEM LETT, V19, P669, DOI 10.1016/j.cclet.2008.04.020