Synthesis of some NH- and NH,S- substituted 1,4-quinones

A series of NH-substituted-1,4-quinones, possessing one, two, three or not chlorine, were synthesized by the reaction between different quinones (p-chloranil (1), p-toluquinone (2), or 2,3-dichloro-1,4-naphthoquinone (3)) and (-)-cis-myrtanylamine (5) via nucleophilic reactions. Moreover, 2-bromo-1,4-naphthoquinone (4) was reacted with 2-(methylthio)ethylamine (11) to produce aminosubstituted naphthoquinones (12 and 13), bearing with bromine and not bromine. In addition, 2-bromo-1,4-naphthoquinone (4) was reacted with 4′-aminodibenzo-18-crown-6 (14) and 4′-aminobenzo-18-crown-6 (16) to yield crown-containing 1,4-naphthoquinones (15 and 17), respectively. New compounds were characterized, providing 1H NMR, 13C NMR, FTIR, MS-ESI, UV/Vis and elemental analysis.

Keywords:

Quinones, amines, p-chloranil, p-toluquinone, 2, 3-dichloro-1 4-naphthoquinone,

PDF

___

Barbosa LCA, 2010, MOLECULES, V15, P5629, DOI 10.3390/molecules15085629
Babula P, 2014, PLANT PHYSIOL BIOCH, V84, P78, DOI 10.1016/j.plaphy.2014.08.027
Bao N, 2017, EUR J MED CHEM, V137, P88, DOI 10.1016/j.ejmech.2017.05.046
Bayen S, 2007, DYES PIGMENTS, V75, P770, DOI 10.1016/j.dyepig.2006.07.033
Bayrak N, 2017, LETT DRUG DES DISCOV, V14, P647, DOI 10.2174/1570180813666161020164931
Bayrak N, 2014, CR CHIM, V17, P563, DOI 10.1016/j.crci.2013.10.022
BUCKLEY D, 1957, J CHEM SOC, P4891, DOI 10.1039/jr9570004891
CAMERON DW, 1964, J CHEM SOC, P4565, DOI 10.1039/jr9640004565
CAMERON DW, 1964, J CHEM SOC, P42, DOI 10.1039/jr9640000042
Delarmelina M, 2015, J BRAZIL CHEM SOC, V26, P1804, DOI 10.5935/0103-5053.20150157
Deniz NG, 2015, CHEM PHARM BULL, V63, P1029, DOI 10.1248/cpb.c15-00607
Deniz NG, 2015, MONATSH CHEM, V146, P2117, DOI 10.1007/s00706-015-1517-5
Ding YX, 2005, J PHARM PHARMACOL, V57, P111, DOI 10.1211/0022357055119
Gafner S, 1996, PHYTOCHEMISTRY, V42, P1315, DOI 10.1016/0031-9422(96)00135-5
Gautam BPS, 2014, SPECTROCHIM ACTA A, V129, P241, DOI 10.1016/j.saa.2014.02.082
Goksel FS, 2014, PHOSPHORUS SULFUR, V189, P113, DOI 10.1080/10426507.2013.798787
Gunatilaka AAL, 2001, J NAT PROD, V64, P2, DOI 10.1021/np000219r
Ibis C, 2011, EUR J MED CHEM, V46, P5861, DOI 10.1016/j.ejmech.2011.09.048
Kacmaz A, 2020, PHOSPHORUS SULFUR, V195, P43, DOI 10.1080/10426507.2019.1633534
Kacmaz A, 2019, OPEN CHEM, V17, DOI 10.1515/chem-2019-0030
Kacmaz A, 2018, PHOSPHORUS SULFUR, V193, P831, DOI 10.1080/10426507.2018.1514503
Kacmaz A, 2018, CHEMISTRYSELECT, V3, P8615, DOI 10.1002/slct.201801155
Kadela-Tomanek M, 2017, MOLECULES, V22, DOI 10.3390/molecules22030447
Katritzky AR, 2008, SYNTHESIS-STUTTGART, P777, DOI 10.1055/s-2008-1032186
Kumagai Y, 2012, ANNU REV PHARMACOL, V52, P221, DOI 10.1146/annurev-pharmtox-010611-134517
KUMANOTANI J, 1968, B CHEM SOC JPN, V41, P2118, DOI 10.1246/bcsj.41.2118
KUTYREV AA, 1991, TETRAHEDRON, V47, P8043, DOI 10.1016/S0040-4020(01)91002-6
Lana EJL, 2006, J AGR FOOD CHEM, V54, P2053, DOI 10.1021/jf052407z
LUBENETS EG, 1994, RUSS CHEM B+, V43, P410, DOI 10.1007/BF01169717
Martinez-Cifuentes M, 2014, AUST J CHEM, V67, P217, DOI 10.1071/CH13355
Martyanov TP, 2012, RUSS CHEM B+, V61, P2282, DOI 10.1007/s11172-012-0323-z
MONKS TJ, 1992, TOXICOL APPL PHARM, V112, P2, DOI 10.1016/0041-008X(92)90273-U
MORI K, 1987, CHEM PHARM BULL, V35, P1270
Neckers L, 1999, INVEST NEW DRUG, V17, P361, DOI 10.1023/A:1006382320697
NISHINA A, 1991, AGR BIOL CHEM TOKYO, V55, P2395, DOI 10.1080/00021369.1991.10870973
Norcott P, 2012, GREEN CHEM, V14, P605, DOI 10.1039/c2gc16259h
Opitz W, 1986, U.S. Patent, Patent No. [4,628,062, 4628062]
Pal S, 2013, J MOL STRUCT, V1049, P355, DOI 10.1016/j.molstruc.2013.06.062
Papageorgiou VP, 1999, ANGEW CHEM INT EDIT, V38, P270, DOI 10.1002/(SICI)1521-3773(19990201)38:3<270::AID-ANIE270>3.0.CO;2-0
Ryu Chung-Kyu, 1992, Archives of Pharmacal Research (Seoul), V15, P263, DOI 10.1007/BF02974067
Ryu CK, 1999, BIOORG MED CHEM LETT, V9, P1075, DOI 10.1016/S0960-894X(99)00152-3
Satheshkumar A, 2014, NEW J CHEM, V38, P993, DOI 10.1039/c3nj01228j
Satheshkumar A, 2012, SPECTROCHIM ACTA A, V98, P378, DOI 10.1016/j.saa.2012.08.056
Silva MG, 2013, J BRAZIL CHEM SOC, V24, P1420, DOI 10.5935/0103-5053.20130180
Silva TMS, 2005, BIOORGAN MED CHEM, V13, P193, DOI 10.1016/j.bmc.2004.09.043
Singh D, 2015, SOLID STATE SCI, V45, P35, DOI 10.1016/j.solidstatesciences.2015.04.004
Siraki AG, 2004, TOXICOL SCI, V81, P148, DOI 10.1093/toxsci/kfh182
SMITH RE, 1984, ANAL CHEM, V56, P2345, DOI 10.1021/ac00277a019
Tandon VK, 2014, RSC ADV, V4, P12441, DOI 10.1039/c3ra47720g
Tandon VK, 2010, TETRAHEDRON LETT, V51, P3843, DOI 10.1016/j.tetlet.2010.05.071
Tandon VK, 2009, TETRAHEDRON LETT, V50, P5896, DOI 10.1016/j.tetlet.2009.07.149
Tapia RA, 2009, J BRAZIL CHEM SOC, V20, P999, DOI 10.1590/S0103-50532009000500027
Tran T, 2004, BIOORGAN MED CHEM, V12, P4809, DOI 10.1016/j.bmc.2004.07.015
Tudor G, 2003, BIOCHEM PHARMACOL, V65, P1061, DOI 10.1016/S0006-2952(03)00013-3
Valderrama JA, 2008, BIOORGAN MED CHEM, V16, P3687, DOI 10.1016/j.bmc.2008.02.018
Wu H, 2008, J ORG CHEM, V73, P4271, DOI 10.1021/jo800581t
Yildirim H, 2017, RSC ADV, V7, P25753, DOI 10.1039/c7ra00868f
YOGO M, 1991, CHEM PHARM BULL, V39, P328
YOSHIHIRA K, 1968, CHEM PHARM BULL, V16, P2383
You ZL, 2012, BIOORGAN MED CHEM, V20, P4889, DOI 10.1016/j.bmc.2012.07.002

ISSN: 1300-0527
Yayın Aralığı: Yılda 6 Sayı
Yayıncı: TÜBİTAK

Arşiv