Copyright (c) 2024 Shruthika D. Rakhe, Shreyas S. Mahurkar, Rahul A. More, Baliram D. Kamale, Manisha P. Munde, Tukaram E. Khatke, Jaman A. Angulwar
This work is licensed under a Creative Commons Attribution 4.0 International License.
Tetrabutylammonium Hydrogen Sulfate (TBAHS) Catalyzed Microwave-Assisted Synthesis of 3,4,5,6,7,9-Hexahydro-1H-xanthene-1,8-(2H)-dione Derivatives and its Biological Study
Corresponding Author(s) : Jaman A. Angulwar
Asian Journal of Chemistry,
Vol. 36 No. 10 (2024): Vol 36 Issue 10, 2024
Abstract
In this study, a facile and eco-friendly synthesis of novel 3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione derivatives using tetrabutylammonium hydrogen sulfate (TBAHS) as a catalyst in the microwave reactor is presented. The reaction involved the condensation of aromatic aldehydes with 1,3-cyclohexanedione in ethanol as solvent, offering significant advantages in terms of reaction rate, yield and purity. The use of TBAHS as catalyst in conjunction with microwave irradiation facilitated the formation of the target xanthene derivatives in remarkably short reaction times. Moreover, Monowave 50 microwave reactor provided precise control over reaction parameters, enabling rapid optimization of reaction conditions. Further these synthesized compounds were systematically evaluated for their antibacterial, antituberculosis and antioxidant activities.
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- C.C. Lai, T.P. Shih, W.C. Ko, H.J. Tang and P.R. Hsueh, Int. J. Antimicrob. Agents, 55, 105924 (2020); https://doi.org/10.1016/j.ijantimicag.2020.105924
- K. Martina, G. Cravotto and R.S. Varma, J. Org. Chem., 86, 13857 (2021); https://doi.org/10.1021/acs.joc.1c00865
- J.M. Jamison, K. Krabill, A. Hatwalkar, E. Jamison and C.C. Tsai, Cell Biol. Int. Rep., 14, 1075 (1990); https://doi.org/10.1016/0309-1651(90)90015-q
- A.A. Napoleon and F.-R.N. Khan, Med. Chem. Res., 23, 4749 (2014); https://doi.org/10.1007/s00044-014-1033-x
- H. Wang, L. Lu, S. Zhu, Y. Li and W. Cai, Curr. Microbiol., 52, 1 (2006); https://doi.org/10.1007/s00284-005-0040-z
- J.J. Omolo, M.M. Johnson, S.F. Van Vuuren and C.B. De Koning, Bioorg. Med. Chem. Lett., 21, 7085 (2011); https://doi.org/10.1016/j.bmcl.2011.09.088
- N. Mulakayala, P.V.N.S. Murthy, D. Rambabu, M. Aeluri, R. Adepu, G.R. Krishna, C.M. Reddy, K.R.S. Prasad, M. Chaitanya, C.S. Kumar, M.V. Basaveswara Rao and M. Pal, Bioorg. Med. Chem. Lett., 22, 2186 (2012); https://doi.org/10.1016/j.bmcl.2012.01.126
- V. Vijayakurup, S. Carmela, D. Carmelo, T. Corrado, P. Srinivas and S. Gopala, Life Sci., 91, 1336 (2012); https://doi.org/10.1016/j.lfs.2012.10.013
- R. Sangwan, M. Saini, R. Verma, S. Kumar, M. Banerjee and S. Jain, J. Mol. Struct., 1208, 127786 (2020); https://doi.org/10.1016/j.molstruc.2020.127786
- K. Chibale, M. Visser, D. van Schalkwyk, P.J. Smith, A. Saravanamuthu and A.H. Fairlamb, Tetrahedron, 59, 2289 (2003); https://doi.org/10.1016/S0040-4020(03)00240-0
- A. Ebadi, A. Karimi, A. Bahmani, Z. Najafi and G. Chehardoli, J. Chem., 2024, 6612503 (2024); https://doi.org/10.1155/2024/6612503
- G. Saint-Ruf, Huynh-Trong-Hieu and J.-P. Poupelin, Naturwissenschaften, 62, 584 (1975); https://doi.org/10.1007/BF01166986
- R.M. Ion, A. Planner, K. Wiktorowicz and D. Frackowiak, Acta Biochim. Pol., 45, 833 (1998).
- A. Naya, M. Ishikawa, K. Matsuda, K. Ohwaki, T. Saeki, K. Noguchi and N. Ohtake, Bioorg. Med. Chem., 11, 875 (2003); https://doi.org/10.1016/S0968-0896(02)00559-X
- M. Manikanttha, K. Deepti, M.B. Tej, A.G. Reddy, R. Kapavarapu, M.V.B. Rao and M. Pal, J. Mol. Struct., 1264, 133313 (2022); https://doi.org/10.1016/j.molstruc.2022.133313
- P. Iniyavan, S. Sarveswari and V. Vijayakumar, Tetrahedron Lett., 56, 1401 (2015); https://doi.org/10.1016/j.tetlet.2015.01.162
- R. Singla, K.B. Gupta, S. Upadhyay, M. Dhiman and V. Jaitak, Bioorg. Med. Chem., 26, 266 (2018); https://doi.org/10.1016/j.bmc.2017.11.040
- O. Deo, S. Alvi, V. Pham, A. Christopoulos, D.M. Thal, B. Capuano, M. Jorg, C. Valant and P.J. Scammells, J. Med. Chem., 65, 12367 (2022); https://doi.org/10.1021/acs.jmedchem.2c01061
- P. Kushwaha, A.K. Tripathi, S. Gupta, P. Kothari, A. Upadhyay, N. Ahmad, T. Sharma, M.I. Siddiqi, R. Trivedi and K.V. Sashidhara, Eur. J. Med. Chem., 156, 103 (2018); https://doi.org/10.1016/j.ejmech.2018.06.062
- M. Nisar, I. Ali, M. Raza Shah, A. Badshah, M. Qayum, H. Khan, I. Khan and S. Ali, RSC Adv., 3, 21753 (2013); https://doi.org/10.1039/c3ra43506g
- A. Kumar, S. Sharma, R.A. Maurya and J. Sarkar, J. Comb. Chem., 12, 20 (2010); https://doi.org/10.1021/cc900143h
- F. Shaheen, M. Ahmad, S.N. Khan, S.S. Hussain, B. Tashkhodjaev, S. Anjum, K. Turgunov, M.N. Sultankhodzhaev, M.I. Choudhary and Atta-ur-Rahman, Eur. J. Org. Chem., 10, 2371 (2006); https://doi.org/10.1002/ejoc.200500936
- X. Chen, T. Pradhan, F. Wang, J.S. Kim and J. Yoon, Chem. Rev., 112, 1910 (2012); https://doi.org/10.1021/cr200201z
- K. Pourshamsian, MethodsX, 9, 101832 (2022); https://doi.org/10.1016/j.mex.2022.101832
- K. Hoseinzade, S.A. Mousavi-Mashhadi and A. Shiri, Mol. Divers., 26, 2745 (2022); https://doi.org/10.1007/s11030-021-10368-3
- A.F. Darweesh, S.K. Salama, I.A. Abdelhamid and A.H.M. Elwahy, Synth. Commun., 51, 471 (2021); https://doi.org/10.1080/00397911.2020.1837170
- Y. Merroun, S. Chehab, A. Hallaoui, T. Guedira, S. Boukhris, A. Souizi and R. Ghailane, J. Mol. Struct., 1294, 136554 (2023); https://doi.org/10.1016/j.molstruc.2023.136554
- F. Rajabi, M. Abdollahi, E.S. Diarjani, M.G. Osmolowsky, O.M. Osmolovskaya, P. Gomez-Lopez, A.R. Puente-Santiago and R. Luque, Materials, 12, 2386 (2019); https://doi.org/10.3390/ma12152386
- N.S. Mehr, S. Abdolmohammadi and M. Afsharpour, Comb. Chem. High Throughput Screen., 24, 683 (2021); https://doi.org/10.2174/1386207323666200924111602
- S. Abdolmohammadi, H. Shahrokhi and S. Dahi-Azar, Polycycl. Arom. Comp., 44, 418 (2024); https://doi.org/10.1080/10406638.2023.2174993
- D. Bhattacharjee, D. Sutradhar, A.K. Chandra and B. Myrboh, Tetrahedron, 73, 3497 (2017); https://doi.org/10.1016/j.tet.2017.05.025
- S.A. Shaikh, V.S. Kamble, S.T. Salunkhe, S.K. Patil and B.D. Aghav, Org. Prep. Proced. Int., 55, 393 (2023); https://doi.org/10.1080/00304948.2023.2169542
- F. Rajabi, M.P. Dios, M. Abdollahi and R. Luque, Catal. Commun., 120, 95 (2019); https://doi.org/10.1016/j.catcom.2018.10.004
- G. Karthikeyan and A. Pandurangan, J. Mol. Catal. Chem., 311, 36 (2009); https://doi.org/10.1016/j.molcata.2009.06.020
- Y. Merroun, S. Chehab, A. Hallaoui, T. Guedira, S. Boukhris, R. Ghailane and A. Souizi, Polycycl. Aromat Compd., 44, 4349 (2024); https://doi.org/10.1080/10406638.2023.2247128
- S. Sheikh, M.A. Nasseri, M. Chahkandi, A. Allahresani and O. Reiser, J. Hazard. Mater., 400, 122985 (2020); https://doi.org/10.1016/j.jhazmat.2020.122985
- B. Maleki, E. Akbarzadeh and S. Babaee, Dyes Pigments, 123, 222 (2015); https://doi.org/10.1016/j.dyepig.2015.08.009
- S. Makone and S. Mahurkar, Green Sustainable Chem., 3, 27 (2013); https://doi.org/10.4236/gsc.2013.34A005
- A. Samani, S. Abdolmohammadi and A. Otaredi-Kashani, Comb. Chem. High Throughput Screen., 21, 111 (2018); https://doi.org/10.2174/1386207321666180219151705
- E. Davoodi, E. Tahanpesar and A.R. Massah, J. Chem. Sci., 134, 72 (2022); https://doi.org/10.1007/s12039-022-02065-x
- R. Rahnamafar, L. Moradi and M. Khoobi, J. Heterocycl. Chem., 57, 1825 (2020); https://doi.org/10.1002/jhet.3911
- B. Teli, M.M. Mubarak, Z. Ahmad and B.A. Bhat, RSC Med. Chem. (2024); https://doi.org/10.1039/D3MD00518F
- H.B. El-Nassan, S.S. El-Mosallamy and A.M. Mahmoud, Sustain. Chem. Pharm., 35, 101207 (2023); https://doi.org/10.1016/j.scp.2023.101207
- L. Amiri-Zirtol and M.A. Amrollahi, Polycycl. Aromat. Compd., 42, 5696 (2022); https://doi.org/10.1080/10406638.2021.1954039
- S. Zukic, E. Veljovic, S. Spirtovic-Halilovic, A. Osmanovic, S. Muratovic, S. Trifunovic, I. Novakovic and D. Zavrsnik, Croat. Chem. Acta, 91, 1 (2018); https://doi.org/10.5562/cca3225
- L. Li-Bin, J. Tong-Shou, H. Li-Sha, L. Meng, Q. Na and L. Tong-Shuang, E-J. Chem., 3, 117 (2006); https://doi.org/10.1155/2006/686538
- B. Maleki, S. Barzegar, Z. Sepehr, M. Kermanian and R. Tayebee, J Iran Chem Soc, 9, 757 (2012); https://doi.org/10.1007/s13738-012-0092-5
- A. John, P.J.P. Yadav and S. Palaniappan, J. Mol. Catal. Chem., 248, 121 (2006); https://doi.org/10.1016/j.molcata.2005.12.017
- F. Shirini, M. Abedini and R. Pourhasan, Dyes Pigments, 99, 250 (2013); https://doi.org/10.1016/j.dyepig.2013.04.036
- S. Kamble, G. Rashinkar, A. Kumbhar and R. Salunkhe, Green Chem. Lett. Rev., 5, 101 (2012); https://doi.org/10.1080/17518253.2011.584217
- H.B. El-Nassan, S.S. El-Mosallamy and A.M. Mahmoud, Sustain. Chem. Pharm., 35, 101207 (2003); https://doi.org/10.1016/j.scp.2023.101207
- G.G. Mandawad, R.D. Kamble, S.V. Hese, R.A. More, R.N. Gacche, K.M. Kodam and B.S. Dawane, Med. Chem. Res., 23, 4455 (2014); https://doi.org/10.1007/s00044-014-1016-y
- S.S. Mahurkar, S.S. Makone and R.A. More, Chem. Biol. Interact., 9, 277 (2019).
- R. More, G. Sanap, A. Siddiqui, S. Dhutekar, S. Patil, V. Diwan, M. Lokare, A. Ingle and P. Maske, World J. Pharm. Res., 9, 892 (2018).
- R.A. More, G.B. Sanap, M.A. Karale, Y.P. Sarnikar and R.N. Gacche, Indian J. Public Health Res. Dev., 11, 607 (2020).
- S.D. Rakhe, S.S. Mahurkar, R.A. More, A.V. Deshmukh, B.D. Kamale and J.A. Angulwar, Russ. J. Org. Chem., 60, 723 (2024); https://doi.org/10.1134/S1070428024040225
References
C.C. Lai, T.P. Shih, W.C. Ko, H.J. Tang and P.R. Hsueh, Int. J. Antimicrob. Agents, 55, 105924 (2020); https://doi.org/10.1016/j.ijantimicag.2020.105924
K. Martina, G. Cravotto and R.S. Varma, J. Org. Chem., 86, 13857 (2021); https://doi.org/10.1021/acs.joc.1c00865
J.M. Jamison, K. Krabill, A. Hatwalkar, E. Jamison and C.C. Tsai, Cell Biol. Int. Rep., 14, 1075 (1990); https://doi.org/10.1016/0309-1651(90)90015-q
A.A. Napoleon and F.-R.N. Khan, Med. Chem. Res., 23, 4749 (2014); https://doi.org/10.1007/s00044-014-1033-x
H. Wang, L. Lu, S. Zhu, Y. Li and W. Cai, Curr. Microbiol., 52, 1 (2006); https://doi.org/10.1007/s00284-005-0040-z
J.J. Omolo, M.M. Johnson, S.F. Van Vuuren and C.B. De Koning, Bioorg. Med. Chem. Lett., 21, 7085 (2011); https://doi.org/10.1016/j.bmcl.2011.09.088
N. Mulakayala, P.V.N.S. Murthy, D. Rambabu, M. Aeluri, R. Adepu, G.R. Krishna, C.M. Reddy, K.R.S. Prasad, M. Chaitanya, C.S. Kumar, M.V. Basaveswara Rao and M. Pal, Bioorg. Med. Chem. Lett., 22, 2186 (2012); https://doi.org/10.1016/j.bmcl.2012.01.126
V. Vijayakurup, S. Carmela, D. Carmelo, T. Corrado, P. Srinivas and S. Gopala, Life Sci., 91, 1336 (2012); https://doi.org/10.1016/j.lfs.2012.10.013
R. Sangwan, M. Saini, R. Verma, S. Kumar, M. Banerjee and S. Jain, J. Mol. Struct., 1208, 127786 (2020); https://doi.org/10.1016/j.molstruc.2020.127786
K. Chibale, M. Visser, D. van Schalkwyk, P.J. Smith, A. Saravanamuthu and A.H. Fairlamb, Tetrahedron, 59, 2289 (2003); https://doi.org/10.1016/S0040-4020(03)00240-0
A. Ebadi, A. Karimi, A. Bahmani, Z. Najafi and G. Chehardoli, J. Chem., 2024, 6612503 (2024); https://doi.org/10.1155/2024/6612503
G. Saint-Ruf, Huynh-Trong-Hieu and J.-P. Poupelin, Naturwissenschaften, 62, 584 (1975); https://doi.org/10.1007/BF01166986
R.M. Ion, A. Planner, K. Wiktorowicz and D. Frackowiak, Acta Biochim. Pol., 45, 833 (1998).
A. Naya, M. Ishikawa, K. Matsuda, K. Ohwaki, T. Saeki, K. Noguchi and N. Ohtake, Bioorg. Med. Chem., 11, 875 (2003); https://doi.org/10.1016/S0968-0896(02)00559-X
M. Manikanttha, K. Deepti, M.B. Tej, A.G. Reddy, R. Kapavarapu, M.V.B. Rao and M. Pal, J. Mol. Struct., 1264, 133313 (2022); https://doi.org/10.1016/j.molstruc.2022.133313
P. Iniyavan, S. Sarveswari and V. Vijayakumar, Tetrahedron Lett., 56, 1401 (2015); https://doi.org/10.1016/j.tetlet.2015.01.162
R. Singla, K.B. Gupta, S. Upadhyay, M. Dhiman and V. Jaitak, Bioorg. Med. Chem., 26, 266 (2018); https://doi.org/10.1016/j.bmc.2017.11.040
O. Deo, S. Alvi, V. Pham, A. Christopoulos, D.M. Thal, B. Capuano, M. Jorg, C. Valant and P.J. Scammells, J. Med. Chem., 65, 12367 (2022); https://doi.org/10.1021/acs.jmedchem.2c01061
P. Kushwaha, A.K. Tripathi, S. Gupta, P. Kothari, A. Upadhyay, N. Ahmad, T. Sharma, M.I. Siddiqi, R. Trivedi and K.V. Sashidhara, Eur. J. Med. Chem., 156, 103 (2018); https://doi.org/10.1016/j.ejmech.2018.06.062
M. Nisar, I. Ali, M. Raza Shah, A. Badshah, M. Qayum, H. Khan, I. Khan and S. Ali, RSC Adv., 3, 21753 (2013); https://doi.org/10.1039/c3ra43506g
A. Kumar, S. Sharma, R.A. Maurya and J. Sarkar, J. Comb. Chem., 12, 20 (2010); https://doi.org/10.1021/cc900143h
F. Shaheen, M. Ahmad, S.N. Khan, S.S. Hussain, B. Tashkhodjaev, S. Anjum, K. Turgunov, M.N. Sultankhodzhaev, M.I. Choudhary and Atta-ur-Rahman, Eur. J. Org. Chem., 10, 2371 (2006); https://doi.org/10.1002/ejoc.200500936
X. Chen, T. Pradhan, F. Wang, J.S. Kim and J. Yoon, Chem. Rev., 112, 1910 (2012); https://doi.org/10.1021/cr200201z
K. Pourshamsian, MethodsX, 9, 101832 (2022); https://doi.org/10.1016/j.mex.2022.101832
K. Hoseinzade, S.A. Mousavi-Mashhadi and A. Shiri, Mol. Divers., 26, 2745 (2022); https://doi.org/10.1007/s11030-021-10368-3
A.F. Darweesh, S.K. Salama, I.A. Abdelhamid and A.H.M. Elwahy, Synth. Commun., 51, 471 (2021); https://doi.org/10.1080/00397911.2020.1837170
Y. Merroun, S. Chehab, A. Hallaoui, T. Guedira, S. Boukhris, A. Souizi and R. Ghailane, J. Mol. Struct., 1294, 136554 (2023); https://doi.org/10.1016/j.molstruc.2023.136554
F. Rajabi, M. Abdollahi, E.S. Diarjani, M.G. Osmolowsky, O.M. Osmolovskaya, P. Gomez-Lopez, A.R. Puente-Santiago and R. Luque, Materials, 12, 2386 (2019); https://doi.org/10.3390/ma12152386
N.S. Mehr, S. Abdolmohammadi and M. Afsharpour, Comb. Chem. High Throughput Screen., 24, 683 (2021); https://doi.org/10.2174/1386207323666200924111602
S. Abdolmohammadi, H. Shahrokhi and S. Dahi-Azar, Polycycl. Arom. Comp., 44, 418 (2024); https://doi.org/10.1080/10406638.2023.2174993
D. Bhattacharjee, D. Sutradhar, A.K. Chandra and B. Myrboh, Tetrahedron, 73, 3497 (2017); https://doi.org/10.1016/j.tet.2017.05.025
S.A. Shaikh, V.S. Kamble, S.T. Salunkhe, S.K. Patil and B.D. Aghav, Org. Prep. Proced. Int., 55, 393 (2023); https://doi.org/10.1080/00304948.2023.2169542
F. Rajabi, M.P. Dios, M. Abdollahi and R. Luque, Catal. Commun., 120, 95 (2019); https://doi.org/10.1016/j.catcom.2018.10.004
G. Karthikeyan and A. Pandurangan, J. Mol. Catal. Chem., 311, 36 (2009); https://doi.org/10.1016/j.molcata.2009.06.020
Y. Merroun, S. Chehab, A. Hallaoui, T. Guedira, S. Boukhris, R. Ghailane and A. Souizi, Polycycl. Aromat Compd., 44, 4349 (2024); https://doi.org/10.1080/10406638.2023.2247128
S. Sheikh, M.A. Nasseri, M. Chahkandi, A. Allahresani and O. Reiser, J. Hazard. Mater., 400, 122985 (2020); https://doi.org/10.1016/j.jhazmat.2020.122985
B. Maleki, E. Akbarzadeh and S. Babaee, Dyes Pigments, 123, 222 (2015); https://doi.org/10.1016/j.dyepig.2015.08.009
S. Makone and S. Mahurkar, Green Sustainable Chem., 3, 27 (2013); https://doi.org/10.4236/gsc.2013.34A005
A. Samani, S. Abdolmohammadi and A. Otaredi-Kashani, Comb. Chem. High Throughput Screen., 21, 111 (2018); https://doi.org/10.2174/1386207321666180219151705
E. Davoodi, E. Tahanpesar and A.R. Massah, J. Chem. Sci., 134, 72 (2022); https://doi.org/10.1007/s12039-022-02065-x
R. Rahnamafar, L. Moradi and M. Khoobi, J. Heterocycl. Chem., 57, 1825 (2020); https://doi.org/10.1002/jhet.3911
B. Teli, M.M. Mubarak, Z. Ahmad and B.A. Bhat, RSC Med. Chem. (2024); https://doi.org/10.1039/D3MD00518F
H.B. El-Nassan, S.S. El-Mosallamy and A.M. Mahmoud, Sustain. Chem. Pharm., 35, 101207 (2023); https://doi.org/10.1016/j.scp.2023.101207
L. Amiri-Zirtol and M.A. Amrollahi, Polycycl. Aromat. Compd., 42, 5696 (2022); https://doi.org/10.1080/10406638.2021.1954039
S. Zukic, E. Veljovic, S. Spirtovic-Halilovic, A. Osmanovic, S. Muratovic, S. Trifunovic, I. Novakovic and D. Zavrsnik, Croat. Chem. Acta, 91, 1 (2018); https://doi.org/10.5562/cca3225
L. Li-Bin, J. Tong-Shou, H. Li-Sha, L. Meng, Q. Na and L. Tong-Shuang, E-J. Chem., 3, 117 (2006); https://doi.org/10.1155/2006/686538
B. Maleki, S. Barzegar, Z. Sepehr, M. Kermanian and R. Tayebee, J Iran Chem Soc, 9, 757 (2012); https://doi.org/10.1007/s13738-012-0092-5
A. John, P.J.P. Yadav and S. Palaniappan, J. Mol. Catal. Chem., 248, 121 (2006); https://doi.org/10.1016/j.molcata.2005.12.017
F. Shirini, M. Abedini and R. Pourhasan, Dyes Pigments, 99, 250 (2013); https://doi.org/10.1016/j.dyepig.2013.04.036
S. Kamble, G. Rashinkar, A. Kumbhar and R. Salunkhe, Green Chem. Lett. Rev., 5, 101 (2012); https://doi.org/10.1080/17518253.2011.584217
H.B. El-Nassan, S.S. El-Mosallamy and A.M. Mahmoud, Sustain. Chem. Pharm., 35, 101207 (2003); https://doi.org/10.1016/j.scp.2023.101207
G.G. Mandawad, R.D. Kamble, S.V. Hese, R.A. More, R.N. Gacche, K.M. Kodam and B.S. Dawane, Med. Chem. Res., 23, 4455 (2014); https://doi.org/10.1007/s00044-014-1016-y
S.S. Mahurkar, S.S. Makone and R.A. More, Chem. Biol. Interact., 9, 277 (2019).
R. More, G. Sanap, A. Siddiqui, S. Dhutekar, S. Patil, V. Diwan, M. Lokare, A. Ingle and P. Maske, World J. Pharm. Res., 9, 892 (2018).
R.A. More, G.B. Sanap, M.A. Karale, Y.P. Sarnikar and R.N. Gacche, Indian J. Public Health Res. Dev., 11, 607 (2020).
S.D. Rakhe, S.S. Mahurkar, R.A. More, A.V. Deshmukh, B.D. Kamale and J.A. Angulwar, Russ. J. Org. Chem., 60, 723 (2024); https://doi.org/10.1134/S1070428024040225