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Letters in Organic Chemistry

Editor-in-Chief

ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

Review Article

Vilsmeier Haack Reaction: An Exemplary Tool for Synthesis of different Heterocycles

Author(s): Shivani Tyagi, Rakhi Mishra*, Avijit Mazumder and Varsha Jindaniya

Volume 21, Issue 2, 2024

Published on: 22 September, 2023

Page: [131 - 148] Pages: 18

DOI: 10.2174/1570178620666230911152937

Price: $65

Abstract

Heterocyclic compounds and their derivatives epitomize the building blocks of many biological entities, e.g., alkaloids, antibiotics, enzymes, hormones, vitamins, and others that are abundant in nature. The Vilsmeier-Haack reaction has fascinated organic chemists due to its significant use in the synthesis of numerous heterocycles. This analytical evaluation provides a scrutinized overview of the literature on the synthesis of heterocyclic compounds.

A comprehensive review of the literature related to Vilsmeier- Haack reagents and reactions is done from PubMed and other sources like google scholar and Google websites.

This precise analytic evaluation provides a revolutionary update on the Vilsmeier-Haack reaction and its applications in the synthesis of natural and synthetic compounds.

Presently researchers are developing and looking for unconventional reagents that are inexpensive, have high chemical yields, are environmentally benign, recyclable, and robust. The information incorporated in this review paper may inspire more research on the Vilsmeier-Haack reagent and its usage in heterocycle synthesis.

Graphical Abstract

[1]
Rajput, A.P.; Girase, P.D. Int. J. Pharm. Chem. Biol. Sci., 2012, 3(1), 25-33.
[2]
Bollyn, M. Org. Process Res. Dev., 2005, 9(6), 982-996.
[http://dx.doi.org/10.1021/op0580116]
[3]
Paul, N.; Muthusubramanian, S. Helv. Chim. Acta, 2013, 96(3), 452-457.
[http://dx.doi.org/10.1002/hlca.201200198]
[4]
Kuznetsov, M.; Ilyin, P.; Pankova, A. Synthesis., 2012, 44(9), 1353-1358.
[http://dx.doi.org/10.1055/s-0031-1290763]
[5]
Zhang, R.; Zhang, D.; Liang, Y.; Zhou, G.; Dong, D. J. Org. Chem., 2011, 76(8), 2880-2883.
[http://dx.doi.org/10.1021/jo101949y] [PMID: 21391701]
[6]
Xiang, D.; Yang, Y.; Zhang, R.; Liang, Y.; Pan, W.; Huang, J.; Dong, D. J. Org. Chem., 2007, 72(22), 8593-8596.
[http://dx.doi.org/10.1021/jo7015482] [PMID: 17915930]
[7]
Ding, S.; Jiao, N. Angew. Chem. Int. Ed., 2012, 51(37), 9226-9237.
[http://dx.doi.org/10.1002/anie.201200859] [PMID: 22930476]
[8]
Rajanna, K.C.; Ferdose, A.; Rajendar, R.K.; Arifuddin, M.; Moazzam, A.M. J. Solution Chem., 2016, 45(3), 371-394.
[http://dx.doi.org/10.1007/s10953-016-0442-5]
[9]
Shan, W.G.; Shi, X.J.; Su, W.K. Org. Prep. Proced. Int., 2009, 36(4), 337.
[10]
Weike, S.; Yiyi, W.; Ling, J.; Yanyan, Y.; Linyao, Z.; Zhiwei, C.; Zhenhua, L.; Jianjun, L. Org. Prep. Proced. Int., 2010, 42(6), 503-555.
[11]
Rajanna, K.C.; Venkateswarku, M.; Satish Kumar, M.; Umesh Kumar, U.; Venkateshwarlu, G.; Saiprakash, P.K. Int. J. Chem. Kinet., 2012, (Dec), 75.
[12]
Chakradhar, A.; Roopa, R.; Rajanna, K.C.; Saiprakash, P.K. Synth. Commun., 1818, 39(10), 1817-1824.
[13]
Sebastiaan, AMW van den Broek; Jeroen, R.L.; Rene, B.; Marielle, M.E.D.; Pieter, J.N.; Kaspar, K.; Floris, PJTR Org. Process Res. Dev., 2012, 16(5), 934-938.
[14]
Roohi, L.; Afghan, A.; Baradarani, M. Curr. Chem. Lett., 2013, 2(4), 187-188.
[15]
Dong, D.; Yingchun, Y.; Yimei, Q.; Zhuo, W.; Qun, L. Synthesis., 2005, 85-91.
[16]
Mohammed, T.; Aejaz, A.K.; Shakeel, S.M.I.; Areej, D.; Kayamkani, A.K.; Muazzam, S.M.; Shaik, H.F. Asian J. Pharm., 2021, 15(3), 365-366.
[17]
Ajith, D.T.; Josemin,; Asokan, C.V. Tetrahedron., 2004, 23, 5069-5076.
[18]
Majid, M.H.; Mahdieh, G.; Leyla, M.K. Royal. Soc. Chem., 2018, 8, 27834-27835.
[19]
Tarik, E. Synth. Commun., 2013, 2013(24), 3329-3341.
[20]
Int. J. Chemtech Res., 2018, 11(03), 183-184.
[21]
Koeller, S.; Lellouche, J-P. Tetrahedron Lett., 1999, 40(38), 7043-7046.
[http://dx.doi.org/10.1016/S0040-4039(99)01453-7]
[22]
Nandha, K.R.; Suresh, T.; Dhanabal, T.; Mohan, P.S. Indian J. Chem., 2004, (Apr), 846.
[23]
Hadjermissoum, Y.D.; Choukchou-Braham, N. The 24th International Electronic Conference on Synthetic Organic Chemistry. 2020, 1.
[24]
Kumari, P.; Sumit, S.; Anil, K.P.; Karan, S. J. Heterocycl. Chem., 2019, 1-3.
[25]
John, T.; Edith, J.B.; Melissa, D.S.; Matthew, B.C.; Jonathan, E.H.; Anastasia, K.; Daniel, C.F.; Ben, C.G.; Kristin, L.S.; Matt, J.K.; Timothy, M.S.; Rene, P.F.K.; Raymond, N.D.; James, A.S. Tetrahedron., 2008, 64, 5246-5247.
[26]
Kantlehner, W. Eur. J. Org. Chem., 2003, 2531-2533.
[27]
Vekateswarlu, M.; Kumar, M.S.; Ramgopal, S.; Kamatala, C.R.; Utkoor, U.K.; Kusampally, U.; Pondichery, K.S. Helv. Chim. Acta, 2011, 94, 2178-2182.
[28]
Aneesa, F.; Rajanna, K.C.; Rajendar Reddy, K.; Moazzam Ali, M.; Arun Kumar, Y. Synth. React. Inorg. Met.-Org. Nano-Met. Chem., 2015, 45(5), 651-659.
[http://dx.doi.org/10.1080/15533174.2013.843545]
[29]
Amin, S. Phosphorus Sulfur Silicon Relat. Elem., 2020, 196(3), 1-64.
[30]
Özpınar, G.A.; Kaufmann, D.E.; Clark, T. J. Mol. Model., 2011, 17(12), 3209-3217.
[http://dx.doi.org/10.1007/s00894-010-0941-z] [PMID: 21365228]
[31]
Jean-Paul, L. J. Org. Chem., 2000, (June), 693-694.
[32]
Venkateswarlu, M.; Rajanna, K.C.; Kumar, M.S.; Kumar, U.U.; Ramgopal, S.; Saiprakash, P.K. Int. J. Org. Chem., 2011, 1(4), 233-241.
[http://dx.doi.org/10.4236/ijoc.2011.14034]
[33]
Charles, M. Tetrahedron., 1992, 48(18), 3659-3726.
[34]
Venkanna, P.; Rajanna, K.C.; Satish, K.M. Tetrahedron Lett., 2015, 56(37), 1-3.
[35]
Duguta, G. Synth. Commun., 2020, 50(11), 1641-1655.
[36]
Govardhan, D.; Bhoosan, M.; Saiprakash, P.K.; Rajanna, K.C.SN Appl. Sci., 2019, 1, 1004.
[37]
Srivastava, V.; Negi, A.S.; Kumar, J.K.; Gupta, M.M. Steroids, 2006, 71(7), 632-638.
[http://dx.doi.org/10.1016/j.steroids.2006.03.005] [PMID: 16704871]
[38]
Aghera, V.K.; Patel, J.P.; Parsania, P.H. ARKIVOC, 2008, 2008(12), 195-204.
[http://dx.doi.org/10.3998/ark.5550190.0009.c21]
[39]
Meng, G.; Sha, Y.W.; Zhang, R.; Bai, N. Chin. Chem. Lett., 2011, 22(9), 1043-1046.
[http://dx.doi.org/10.1016/j.cclet.2011.03.009]
[40]
Duguta, G.; Bhooshan, M.; Chinna, R.K; Yadaiah, C. Chem. Data Collect., 2020, 28, 100382.
[41]
Kimura, Y.; Matsuura, D. Int. J. Org. Chem., 2013, 3(3), 1-7.
[http://dx.doi.org/10.4236/ijoc.2013.33A001]
[42]
Damljanović, I.; Vukićević, M.; Radulović, N.; Palić, R.; Ellmerer, E.; Ratković, Z.; Joksović, M.D.; Vukićević. R.D. Bioorg. Med. Chem. Lett., 2009, 19(4), 1093-1096.
[http://dx.doi.org/10.1016/j.bmcl.2009.01.006] [PMID: 19167220]
[43]
Ivonin, S.P. Chem. Heterocycl. Compd., 2011, 47(8), 1048-1049.
[http://dx.doi.org/10.1007/s10593-011-0873-2]
[44]
Ismail, A. J. Org. Chem., 2021, 162-173.
[45]
Alam, M.; Mushfiq, M. Chin. Chem. Lett., 2008, 19(2), 133-136.
[http://dx.doi.org/10.1016/j.cclet.2007.11.027]
[46]
Maria, A.F. Bioorg. Med. Chem., 2009, 17(1), 295-296.
[47]
Ashok, D.; Devulapally, M.G.; Gundu, S.; Aamate, V.K.; Chintalapally, S. Chem. Heterocycl. Compd., 2016, 52(8), 609-614.
[http://dx.doi.org/10.1007/s10593-016-1939-y]
[48]
Ramu, M. Synlett., 2014, 2176-2178.
[49]
Aleksandr, V J. Org. Chem., 2019, 7, 1-3.
[50]
Asokan, C.V.; Anabha, E.R.; Thomas, A.D.; Jose, A.M.; Lethesh, K.C.; Prasanth, M.; Krishanraj, K.U. Tetrahedron Lett., 2007, 48(32), 5641-5643.
[http://dx.doi.org/10.1016/j.tetlet.2007.06.032]
[51]
Ghodsi, M.Z.; Zohreh, K.; Fatemeh, M.J. Iran. Chem. Soc., 2019, 17, 247-282.
[52]
Yukako, T. Bioorg. Med. Chem., 2009, 17(11), 3959-3967.
[53]
Prakash, O.; Hussain, K.; Deepak, K. Org. Med. Chem. Lett., 2011, 1(1), 1-4.
[http://dx.doi.org/10.1186/2191-2858-1-1] [PMID: 22373059]
[54]
Daniel, L. New J. Chem., 2003, 1670-1671.
[55]
Vorona, M.; Potorocina, I.; Veinberg, G.; Shestakova, I.; Kanepe, I.; Petrova, M.; Leipinsh, E.; Lukevics, E. Chem. Heterocycl. Compd., 2007, 43, 446-448.
[56]
Sandip, B. Bioorg. Med. Chem., 2007, 15(1), 87-96.
[57]
Diana, P.; Carbone, A.; Barraja, P.; Kelter, G.; Fiebig, H.H.; Cirrincione, G. Bioorg. Med. Chem., 2010, 18(12), 4524-4529.
[http://dx.doi.org/10.1016/j.bmc.2010.04.061] [PMID: 20472437]
[58]
Barraja, P.; Diana, P.; Montalbano, A.; Carbone, A.; Cirrincione, G.; Viola, G.; Salvador, A.; Vedaldi, D.; Dall’Acqua, F. Bioorg. Med. Chem., 2008, 16(22), 9668-9683.
[http://dx.doi.org/10.1016/j.bmc.2008.10.002] [PMID: 18951030]
[59]
Alexander, V. Org. Lett., 2015, 17(15), 3734-3737.
[60]
John, T. Tetrahedron., 2008, 64(22), 5246-5250.
[61]
Barman, G. Chem. Heterocycl. Compd., 2015, 51(10), 869-871.
[http://dx.doi.org/10.1007/s10593-015-1789-z]
[62]
Ofitserova, E.S.; Shklyarenko, A.A.; Yakovlev, I.P. Russ. J. Gen. Chem., 2020, 90(4), 750-752.
[http://dx.doi.org/10.1134/S1070363220040301]
[63]
Quiroga, J.; Trilleras, J.; Insuasty, B.; Abonía, R.; Nogueras, M.; Cobo, J. Tetrahedron Lett., 2008, 49(17), 2689-2691.
[http://dx.doi.org/10.1016/j.tetlet.2008.02.166]
[64]
Nagaraju, R.; Gopichand, K.; Rao, N.N.; Ganai, A.M.; Kishan, E.; Rao, P.V. Russ. J. Gen. Chem., 2020, 90(2), 314-318.
[http://dx.doi.org/10.1134/S1070363220020255]
[65]
Arvind, R. Bioorg. Med. Chem. Lett., 2021, 41, 127984.
[66]
Bhooshan, M.; Venkanna, P.; Venkateswarlu, M.; Satish, K.M.; Rajanna, K.C. Synlett., 2017, 29, 85-88.
[67]
Kiran, S. J. Heterocycl. Chem., 2020, 57(4), 1692-1697.
[68]
Hanaa, A Int. J. Res. Pharm. Sci., 2014.
[69]
Jiao, L.; Yu, C.; Li, J.; Wang, Z.; Wu, M.; Hao, E. J. Org. Chem., 2009, 74(19), 7525-7528.
[http://dx.doi.org/10.1021/jo901407h] [PMID: 19722510]
[70]
Eduardo, P.U. Dyes. Pigments., 2017, 141, 286-298.
[71]
Nath, M.; Singh, P. SynOpen, 2020, 4(2), 44-50.
[http://dx.doi.org/10.1055/s-0040-1707429]
[72]
Banerjee, S.; Hyland, M.A.; Brückner, C. Tetrahedron Lett., 2010, 51(34), 4505-4508.
[http://dx.doi.org/10.1016/j.tetlet.2010.06.096]
[73]
Majdouline, R.; Frederic, V.; Julien, M.; Jean-Francois, P. J. Org. Chem., 2018, 83(15), 8731-8738.
[74]
Malose, J. Org. Biomol. Chem., 2019, 17, 2204-2211.
[75]
Bhat, M.; Nagaraja, G.K.; Peethamber, S.K.; Mohammed, S.R. Royal. Soc. Chem., 2016, 59375-59377.
[76]
Noor, Th. Egypt. J. Chem., 2022, 65(6), 685-686.
[77]
Yadav, A.G.; Patil, V.N.; Asrondkar, A.L.; Naik, A.A.; Ansulkar, P.V.; Bobade, A.S.; Chowdhary, A.S. Rasayan J. Chem., 2012, 5(1), 117-120.
[78]
Gao, Y.; Huang, D-C.; Liu, C.; Song, Z-L.; Liu, J-R.; Guo, S-K.; Tan, J-Y.; Qiu, R-L.; Jin, B.; Zhang, H.; Mulholland, N.; Han, X.; Xia, Q.; Ali, A.S.; Guo, D.; Deng, Y.; Gu, Y-C.; Zhang, M-Z. Bioorg. Med. Chem., 2021, 1-10.
[79]
Kaur, R.; Rani, V.; Abbot, V.; Kapoor, Y. J. Chem. Pharm. Sci., 2017, 18, 31.
[80]
Abubakar, M.K. J. Heterocycl. Chem., 2018, 55(2), 492-497.
[81]
Ibrahim-Ouail, M.; Frederic, D. J. Org. Chem., 2019, 2019(1), 304-339.
[82]
Yue, Z. Eur. J. Med. Chem., 2020, 189, 112038.
[83]
Afsina Abdulla, C.M. ChemistrySelect, 2020, 5(33), 10374-10386.
[84]
Senthil Kumar, R.; Praveen, S.; Shridharshini, K.; Maruthamuthu, M.; Mohanapriya, K.; Anjana, E. World J. Pharm. Res., 2022, 11(4), 832-871.
[85]
Roma, A. Tetrahedron Lett., 2017, 58(32), 3139-3142.
[86]
Paul, N.; Muthusubramanian, S. Tetrahedron Lett., 2011, 3745.
[87]
Oleg, K.F.; Anton, V.K.; Svetlana, A.V.; Aleksander, V.M.; Victor, I.M. Monatsh. Chem., 2021, 152, 95.
[88]
Outin, J.; Quellier, P.; Belanger, G. J. Org. Chem., 2019, 85(7), 4712-4729.
[89]
Bera, R.; Swamy, N.K. Tetrahedron, 2007, 63, 13020.
[90]
Te Ali, M.A. Russ. J. Org. Chem., 2020, 56, 845-846.
[http://dx.doi.org/10.1134/S1070428020050188]
[91]
Oleg, K. Tetrahedron., 2019, 75(19), 2832-2842.
[92]
Temizsoy, M.; Sethi, W.; Reinholdt, A.; Schau-Magnussen, M.; Bendix, J.; Hammershoi, A. Royal. Soc. Chem., 2015, 44(42), 18438-18446.
[93]
Dattatraya, H. Org. Chem. Front., 2015, 2, 645-648.
[94]
Barhoumi-Slimi, T.M.; Ben Dhia, M.T.; Nsangou, M.; El Gaied, M.M.; Khaddar, M.R. J. Struct. Chem., 2010, 51(2), 251-257.
[95]
Liu, C.; Hu, J.; Xu, H.; Lu, Z.; Yu, X.; Lin, Z. Chem. Nat. Compd., 2015, 51(2), 306-310.
[http://dx.doi.org/10.1007/s10600-015-1266-z]
[96]
Irfan, M.; Deng, R.; Sumra, I.; Zhu, X-F.; Liu, T.; Zeng, Z. Dyes Pigments, 2020, 184, 108733.
[97]
Boudreault, J.; Lévesque, F.; Bélanger, G. J. Org. Chem., 2016, 81(19), 9247-9268.
[http://dx.doi.org/10.1021/acs.joc.6b01835] [PMID: 27641107]
[98]
Tokarev, S. Mendeleev Commun., 2019, 25(9), 567-569.
[http://dx.doi.org/10.1016/j.mencom.2019.09.030]
[99]
Vania, M. Steroids, 2011, 582-587.
[100]
Nuno, M.M. J. Porphyr. Phthalocyanines, 2011, 15, 652-657.
[http://dx.doi.org/10.1142/S1088424611003586]
[101]
Sumit, S. J. Heterocycl. Chem., 2020, 57(7), 2936-2944.
[102]
Quiroga, J.; Diaz, Y.; Insuasty, B.; Abonıa, R.; Nogueras, M.; Cobo. J. Tetrahedron Lett., 2010, 51(21), 2928-2930.
[http://dx.doi.org/10.1016/j.tetlet.2010.03.117]
[103]
Bhat, M.; Nagaraja, G.K. Royal Soc. Chem., 2016, 6, 59375-59388.
[104]
Kurokawa, M.; Watanabe, T.; Ishikawa, T. Helv. Chim. Acta, 2007, 90(3), 574-587.
[http://dx.doi.org/10.1002/hlca.200790058]
[105]
Castillo, J.C.; Tigreros, A.; Portilla, J. J. Org. Chem., 2018, 83(18), 10887-10897.
[http://dx.doi.org/10.1021/acs.joc.8b01571] [PMID: 30051714]
[106]
Ziba, R.S. J. Heterocycl. Chem., 2020, 1-7.
[107]
Yu, C.; Jiao, L.; Yin, H.; Zhou, J.; Pang, W.; Wu, Y.; Wang, Z.; Yang, G.; Hao, E. Eur. J. Org. Chem., 2011, 2011(28), 5460-5468.
[http://dx.doi.org/10.1002/ejoc.201100736]
[108]
Taniguchi, M.; Balakumar, A.; Fan, D.; McDowell, B.E.; Lindsey, J.S. J. Porphyr. Phthalocyanines, 2005, 9(8), 554-574.
[http://dx.doi.org/10.1142/S1088424605000678]
[109]
Gaspar, A.; Matos, M.J.; Garrido, J.; Uriarte, E.; Borges, F. Chem. Rev., 2013, 114(9), 4960-4992.

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