Abstract
This review describes recent advances that are commonly applied in the synthesis of dialkyl (aryl) α-aminophosphonates containing heterocyclic compounds. The target structures are divided into three categories, which include α-aminophosphonic acids and their diesters bearing a heterocyclic or heteroaryl system at the α-carbon, nitrogen atom, or both. The synthetic protocols based on the Kabachnik-Fields and Pudovik reactions as the main pathways for the construction of these features, besides other miscellaneous methods. This review may be a useful resource for researchers and it will help them to work in this emerging research area.
Graphical Abstract
[http://dx.doi.org/10.1021/ja0651005] [PMID: 17260986]
[http://dx.doi.org/10.1080/10426509108029443]
[http://dx.doi.org/10.1016/j.molstruc.2022.134196] [PMID: 36193287]
[http://dx.doi.org/10.1021/jm00151a005] [PMID: 3510298]
[http://dx.doi.org/10.1016/0960-894X(94)00474-T]
[http://dx.doi.org/10.2174/1568011013354543] [PMID: 12678760]
[http://dx.doi.org/10.1016/j.jes.2022.04.023] [PMID: 36522056]
[http://dx.doi.org/10.1080/10426509908546274]
[http://dx.doi.org/10.1016/j.tetlet.2022.154316]
[http://dx.doi.org/10.1002/ejoc.200200698]
[http://dx.doi.org/10.3998/ark.5550190.p009.112]
[http://dx.doi.org/10.3998/ark.5550190.p009.519]
[http://dx.doi.org/10.1021/jo00104a064]
[http://dx.doi.org/10.1016/j.tet.2008.09.083] [PMID: 20871799]
[http://dx.doi.org/10.2174/138527211795703612]
[http://dx.doi.org/10.1016/j.tet.2012.05.008]
[http://dx.doi.org/10.1055/s-2003-37508]
[http://dx.doi.org/10.1016/j.tetlet.2011.04.112]
[http://dx.doi.org/10.1039/B205747F]
[http://dx.doi.org/10.1016/j.bmcl.2011.02.039] [PMID: 21398120]
[http://dx.doi.org/10.1002/hc.21086]
[http://dx.doi.org/10.1002/slct.202003848]
[http://dx.doi.org/10.1016/j.tetlet.2016.03.033]
[http://dx.doi.org/10.1007/s10562-019-02910-8]
[http://dx.doi.org/10.1016/j.arabjc.2012.11.011]
[http://dx.doi.org/10.1016/j.tet.2018.02.047]
[http://dx.doi.org/10.1080/10426507.2020.1799370]
[http://dx.doi.org/10.1080/15257770.2020.1826516] [PMID: 33030107]
[http://dx.doi.org/10.1055/s-0039-1691599]
[http://dx.doi.org/10.1515/znb-2017-0177]
[http://dx.doi.org/10.1016/j.tetlet.2017.01.022]
[http://dx.doi.org/10.1039/C5RA27064B]
[http://dx.doi.org/10.1039/C5RA13173A]
[http://dx.doi.org/10.1007/s12039-016-1113-1]
[http://dx.doi.org/10.1002/slct.202000855]
[http://dx.doi.org/10.1002/slct.202000486]
[http://dx.doi.org/10.1016/j.arabjc.2011.07.025]
[http://dx.doi.org/10.1080/00397911.2020.1753079]
[http://dx.doi.org/10.1007/s11164-020-04321-6]
[http://dx.doi.org/10.1039/D0RA04533K] [PMID: 35515785]
[http://dx.doi.org/10.1007/s00044-019-02436-z]
[http://dx.doi.org/10.1002/ps.5449] [PMID: 31006964]
[http://dx.doi.org/10.1248/cpb.c16-00622] [PMID: 27725363]
[http://dx.doi.org/10.14233/ajchem.2019.22194]
[http://dx.doi.org/10.1039/C5RA21419J]
[http://dx.doi.org/10.1002/slct.201600070]
[http://dx.doi.org/10.1016/j.sjbs.2020.09.061] [PMID: 33304159]
[http://dx.doi.org/10.1016/j.arabjc.2021.103348]
[http://dx.doi.org/10.1007/s13738-018-1571-0]
[http://dx.doi.org/10.1007/s11030-020-10060-y] [PMID: 32124162]
[http://dx.doi.org/10.24820/ark.5550190.p011.887]
[http://dx.doi.org/10.1002/aoc.5082]
[http://dx.doi.org/10.33945/SAMI/ECC.2020.2.11]
[http://dx.doi.org/10.1080/10426507.2017.1290631]
[http://dx.doi.org/10.3390/ijms17050653] [PMID: 27136538]
[http://dx.doi.org/10.1039/C7MD00098G] [PMID: 30108826]
[http://dx.doi.org/10.1016/j.cclet.2017.02.012]
[http://dx.doi.org/10.1002/jhet.3933]
[http://dx.doi.org/10.1080/10426507.2020.1799366]
[http://dx.doi.org/10.1080/10426507.2018.1455201]
[http://dx.doi.org/10.3998/ark.5550190.p009.563]
[http://dx.doi.org/10.1007/s13738-022-02515-w]
[http://dx.doi.org/10.3390/molecules23081981] [PMID: 30096835]
[http://dx.doi.org/10.1080/07391102.2020.1861981] [PMID: 33345710]
[http://dx.doi.org/10.1002/jhet.2541]
[http://dx.doi.org/10.1007/s11030-018-9877-5] [PMID: 30306393]
[http://dx.doi.org/10.1515/mgmc-2020-0018]
[http://dx.doi.org/10.1007/s00044-019-02411-8]
[http://dx.doi.org/10.2174/1385272822666180404145804]
[http://dx.doi.org/10.1080/10426507.2018.1424163]
[http://dx.doi.org/10.1007/s11030-021-10242-2] [PMID: 34117993]
[http://dx.doi.org/10.1080/10426507.2016.1206101]
[http://dx.doi.org/10.1021/acs.jafc.6b01256] [PMID: 27166879]
[http://dx.doi.org/10.1080/10426507.2016.1192629]
[http://dx.doi.org/10.1016/j.ijbiomac.2020.10.065] [PMID: 33075335]
[http://dx.doi.org/10.1016/j.ijbiomac.2020.06.251] [PMID: 32615220]
[http://dx.doi.org/10.1007/s11144-021-02110-9]
[http://dx.doi.org/10.1080/10426507.2016.1225056]
[http://dx.doi.org/10.1039/D1NJ01861B]
[http://dx.doi.org/10.1016/j.ejmech.2019.07.029] [PMID: 31323616]
[http://dx.doi.org/10.1007/s00706-018-2303-y]
[http://dx.doi.org/10.1016/j.jscs.2017.06.002]
[http://dx.doi.org/10.1002/hc.21325]
[http://dx.doi.org/10.1080/00397911.2021.2020844]
[http://dx.doi.org/10.1134/S107036321809027X]
[http://dx.doi.org/10.1080/00397911.2017.1385083]
[http://dx.doi.org/10.1080/00397911.2021.2007402]
[http://dx.doi.org/10.1080/10426507.2015.1119139]
[http://dx.doi.org/10.1002/slct.201801965]
[http://dx.doi.org/10.1016/j.bioorg.2021.104718] [PMID: 33618257]
[http://dx.doi.org/10.1515/znb-2017-0044]
[http://dx.doi.org/10.1080/10799893.2020.1722166] [PMID: 32019395]
[http://dx.doi.org/10.1016/j.bmcl.2016.01.010] [PMID: 26786699]
[http://dx.doi.org/10.1016/j.saa.2018.07.083] [PMID: 30081271]
[http://dx.doi.org/10.1016/j.molstruc.2018.06.094]
[http://dx.doi.org/10.1002/jhet.4157]
[http://dx.doi.org/10.4236/ijoc.2018.81001]
[http://dx.doi.org/10.1016/j.tetlet.2016.01.001]
[http://dx.doi.org/10.1016/j.molstruc.2016.10.054]
[http://dx.doi.org/10.21608/ejchem.2022.125116.5562]
[http://dx.doi.org/10.1080/10426507.2015.1035379]
[http://dx.doi.org/10.1007/s00044-021-02815-5] [PMID: 34744408]
[http://dx.doi.org/10.1016/j.cclet.2016.01.046]
[http://dx.doi.org/10.1002/jhet.3813]
[http://dx.doi.org/10.1080/10426507.2018.1487969]
[http://dx.doi.org/10.1007/s13738-019-01849-2]