Synthesis and characterization of piperazine-substituted dihydrofuran derivatives viaMn(OAc)3 mediated radical cyclizations

The aim of this study is to synthesize novel piperazine-containing dihydrofuran compounds (3a-n)from radical additions and cyclizations of diacyl and alkyl-acyl piperazine derivatives (1a-h) with 1,3-dicarbonyl compounds (2a-c) mediated by Mn(OAc)(3) for the first time. From the reactions of 1a-c with dimedone (2a);1a, 1c, and 1d with acetylacetone (2b); and la with ethylacetoacetate(2c) ,the dihydrofuran-piperazine compounds 3a-c > 3d-f, and 3g were obtained in medium to high yields (31%-81%), respectively. In addition, dihydrofuran-piperazine compounds 3h-j and 3k-n were prepared at low to medium yields (20%-40%) from the reactions of le-g with 2a and 1e-h with 2c, respectively.

Keywords:

Piperazine, dihydrofuran Mn(OAc)3, radical cyclization,

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Appendino G, 1998, TETRAHEDRON, V54, P10819, DOI 10.1016/S0040-4020(98)00621-8
Aslan H, 2017, TETRAHEDRON, V73, P7223, DOI 10.1016/j.tet.2017.11.015
Burgaz EV, 2007, TETRAHEDRON, V63, P7229, DOI 10.1016/j.tet.2007.04.088
Burka JM, 2005, AM J OPHTHALMOL, V140, P83, DOI 10.1016/j.ajo.2005.02.037
Castro S, 2016, CHEM-EUR J, V22, P9068, DOI 10.1002/chem.201601482
Chaudhary P, 2006, BIOORGAN MED CHEM, V14, P1819, DOI 10.1016/j.bmc.2005.10.032
Chen SP, 2012, B CHEM SOC JPN, V85, P920, DOI 10.1246/bcsj.20120100
Chuang CP, 2004, TETRAHEDRON, V60, P1841, DOI 10.1016/j.tet.2003.12.035
Dua R., 2011, ADV BIOL RES, V5, P120 .
Hagiwara H, 2001, J CHEM SOC PERK T 1, P2946, DOI 10.1039/b107180g
Harish KP, 2013, EUR J MED CHEM, V65, P276, DOI 10.1016/j.ejmech.2013.04.054
Hatnapure GD, 2012, BIOORG MED CHEM LETT, V22, P6385, DOI 10.1016/j.bmcl.2012.08.071
Hocaoglu B, 2019, SYNTHETIC COMMUN, V49, P1938, DOI 10.1080/00397911.2019.1611858
Hu CA, 2010, LETT DRUG DES DISCOV, V7, P661, DOI 10.2174/157018010792929595
Kakwani MD, 2011, BIOORG MED CHEM LETT, V21, P1997, DOI 10.1016/j.bmcl.2011.02.022
Kapanda CN, 2012, J MED CHEM, V55, P5774, DOI 10.1021/jm3006004
Kobayashi K, 2003, HETEROCYCLES, V60, P939, DOI 10.3987/COM-02-9690
Kornsakulkarn J, 2012, TETRAHEDRON, V68, P8480, DOI 10.1016/j.tet.2012.07.059
Lallemand JY, 2002, EUR J ORG CHEM, V2002, P503, DOI 10.1002/1099-0690(20022)2002:3<503::AID-EJOC503>3.0.CO;2-6
Lofstrand VA, 2016, TETRAHEDRON, V72, P3775, DOI 10.1016/j.tet.2016.03.012
Lue TF, 2000, NEW ENGL J MED, V342, P1802, DOI 10.1056/NEJM200006153422407
Martinet S, 2007, MAGN RESON CHEM, V45, P182, DOI 10.1002/mrc.1933
Meena P, 2015, BIOORGAN MED CHEM, V23, P1135, DOI 10.1016/j.bmc.2014.12.057
MELIKYAN GG, 1993, SYNTHESIS-STUTTGART, P833, DOI 10.1055/s-1993-25951
Mondal M, 2013, RSC ADV, V3, P18716, DOI 10.1039/c3ra42480d
Nair V, 2006, TETRAHEDRON LETT, V47, P2803, DOI 10.1016/j.tetlet.2006.02.051
Nair V, 2007, CHEM REV, V107, P1862, DOI 10.1021/cr068408n
Ozgur M, 2019, NEW J CHEM, V43, P5737, DOI 10.1039/c9nj00054b
Patel KN, 2014, EUR J MED CHEM, V75, P43, DOI 10.1016/j.ejmech.2014.01.024
Piemontese L, 2018, J ENZYM INHIB MED CH, V33, P1212, DOI 10.1080/14756366.2018.1491564
Rachakonda V, 2013, EUR J MED CHEM, V70, P536, DOI 10.1016/j.ejmech.2013.10.034
Reddy TS, 2012, BIOORG MED CHEM LETT, V22, P4900, DOI 10.1016/j.bmcl.2012.04.133
Saadeh HA, 2009, MOLECULES, V14, P1483, DOI 10.3390/molecules14041483
Sari S, 2019, TURK J CHEM, V43, P1656, DOI 10.3906/kim-1907-16
Snider BB, 1996, CHEM REV, V96, P339, DOI 10.1021/cr950026m
Sridharan V, 2010, CHEM REV, V110, P3805, DOI 10.1021/cr100004p
Stegmeier F, 2010, CLIN PHARMACOL THER, V87, P543, DOI 10.1038/clpt.2009.297
Szabo M, 2014, J MED CHEM, V57, P4924, DOI 10.1021/jm500457x
Huynh TT, 2017, TETRAHEDRON LETT, V58, P3619, DOI 10.1016/j.tetlet.2017.08.002
Tugrak M, 2019, BIOORG CHEM, V90, DOI 10.1016/j.bioorg.2019.103095
Ustalar A, 2017, TURK J CHEM, V41, P80, DOI 10.3906/kim-1604-22
VACCA JP, 1994, P NATL ACAD SCI USA, V91, P4096, DOI 10.1073/pnas.91.9.4096
Vinosha B, 2012, TETRAHEDRON LETT, V53, P962, DOI 10.1016/j.tetlet.2011.12.047
Wang T, 2009, BIOORG MED CHEM LETT, V19, P5140, DOI 10.1016/j.bmcl.2009.07.076
Yilmaz EVB, 2011, ARKIVOC, P363, DOI 10.3998/ark.5550190.0012.230
Yilmaz M, 2005, TETRAHEDRON, V61, P8860, DOI 10.1016/j.tet.2005.07.019
Yilmaz M, 2001, SYNTHETIC COMMUN, V31, P3871, DOI 10.1081/SCC-100108239
Yilmaz M, 2001, SYNTHETIC COMMUN, V31, P2189, DOI 10.1081/SCC-100104471
Yilmaz M, 2016, ARKIVOC, P79, DOI 10.3998/ark.5550190.p009.855
Yilmaz M, 2016, ARKIVOC, P202, DOI 10.3998/ark.5550190.p009.455
Yilmaz M, 2014, ARKIVOC, P225, DOI 10.3998/ark.5550190.p008.482
Yilmaz M, 2011, HELV CHIM ACTA, V94, P2027, DOI 10.1002/hlca.201100105
Yilmaz M, 2011, TETRAHEDRON, V67, P8255, DOI 10.1016/j.tet.2011.08.098
Yilmaz M, 2011, HELV CHIM ACTA, V94, P1335
Yu H., 2012, SCI REP, V2, P1, DOI DOI 10.1038/SREP00772
Zhang PZ, 2017, ORG LETT, V19, P5537, DOI 10.1021/acs.orglett.7b02621
Zhong Y, 2014, S AFR J CHEM-S-AFR T, V67, P214