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Using Homoenolate Annulated Products for Synthesis of Indole Embedded Derivatives
Corresponding Author(s) : Rony Rajan Paul
Asian Journal of Chemistry,
Vol. 33 No. 2 (2021): Vol 33 Issue 2
Abstract
The facile transformation of the functionalized spiro-cyclopentanones obtained by N-heterocyclic carbenes (NHC) catalyzed homoenolate annulation strategy, leading to the synthesis of indole embedded compounds is described.
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- V. Nair, S. Bindu and V. Sreekumar, Angew. Chem. Int. Ed., 43, 5130 (2004);https://doi.org/10.1002/anie.200301714
- V. Nair, S. Vellalath and B.P. Babu, Chem. Soc. Rev., 37, 2691 (2008);https://doi.org/10.1039/b719083m
- J.L. Moore and T. Rovis, Top. Curr. Chem., 291, 77 (2009);https://doi.org/10.1007/128_2008_18
- V. Nair, R.S. Menon, A.T. Biju, C.R. Sinu, R.R. Paul, A. Jose and V. Sreekumar, Chem. Soc. Rev., 40, 5336 (2011);https://doi.org/10.1039/c1cs15139h
- X. Bugaut and F. Glorius, Chem. Soc. Rev., 41, 3511 (2012);https://doi.org/10.1039/c2cs15333e
- R.S. Menon, A.T. Biju and V. Nair, Chem. Soc. Rev., 44, 5040 (2015);https://doi.org/10.1039/C5CS00162E
- D.M. Flanigan, F. Romanov-Michailidis, N.A. White and T. Rovis, Chem. Rev., 115, 9307 (2015);https://doi.org/10.1021/acs.chemrev.5b00060
- M.H. Wang and K.A. Scheidt, Angew. Chem. Int. Ed., 55, 14912 (2016);https://doi.org/10.1002/anie.201605319
- R.S. Menon, A.T. Biju and V. Nair, Beilstein J. Org. Chem., 12, 444 (2016);https://doi.org/10.3762/bjoc.12.47
- K. Zeitler, Angew. Chem. Int. Ed., 44, 7506 (2005);https://doi.org/10.1002/anie.200502617
- A. Grossmann and D. Enders, Angew. Chem. Int. Ed., 51, 314 (2012);https://doi.org/10.1002/anie.201105415
- S.J. Ryan, L. Candish and D.W. Lupton, Chem. Soc. Rev., 42, 4906 (2013);https://doi.org/10.1039/c3cs35522e
- X.-Y. Chen and S. Ye, Org. Biomol. Chem., 11, 7991 (2013);https://doi.org/10.1039/c3ob41469h
- S. Ye and X.-Y. Chen, Synlett, 24, 1614 (2013);https://doi.org/10.1055/s-0033-1339300
- M.N. Hopkinson, C. Richter, M. Schedler and F. Glorius, Nature, 510, 485 (2014);https://doi.org/10.1038/nature13384
- A. Nickon and J.L. Lambert, J. Am. Chem. Soc., 84, 4604 (1962);https://doi.org/10.1021/ja00882a055
- E. Nakamura and I. Kuwajima, J. Am. Chem. Soc., 99, 7360 (1977);https://doi.org/10.1021/ja00464a048
- S. De Lombaert, B. Lesur and L. Ghosez, Tetrahedron Lett., 23, 4251 (1982);https://doi.org/10.1016/S0040-4039(00)88717-1
- M.R. Binns and R.K. Haynes, J. Org. Chem., 46, 3790 (1981);https://doi.org/10.1021/jo00332a005
- S.E. Schaus, J. Branalt and E.N. Jacobsen, J. Org. Chem., 63, 403 (1998);https://doi.org/10.1021/jo971758c
- H. Ahlbrecht, G. Bonnet, D. Enders and M. Zimmermann, Tetrahedron Lett., 21, 3175 (1980);https://doi.org/10.1016/S0040-4039(00)77438-7
- S.S. Sohn, E.L. Rosen and J.W. Bode, J. Am. Chem. Soc., 126, 14370 (2004);https://doi.org/10.1021/ja044714b
- C. Burstein and F. Glorius, Angew. Chem. Int. Ed., 43, 6205 (2004);https://doi.org/10.1002/anie.200461572
- I. Kuwajima and E. Nakamura, eds.: B.M. Trost and I. Fleming, Compre-hensive Organic Synthesis, Pergamon, New York, vol. 2, p. 441 (1991).
- V.J. Lee, eds.: B.M. Trost and I. Fleming, Comprehensive Organic Synthesis, Pergamon: New York, vol. 4, p. 117 (1991).
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- A. Chan and K.A. Scheidt, J. Am. Chem. Soc., 130, 2740 (2008);https://doi.org/10.1021/ja711130p
- V. Nair, V. Varghese, B.P. Babu, C.R. Sinu and E. Suresh, Org. Biomol. Chem., 8, 761 (2010);https://doi.org/10.1039/b922981g
- M. He and J.W. Bode, Org. Lett., 7, 3131 (2005);https://doi.org/10.1021/ol051234w
- D.E.A. Raup, B. Cardinal-David, D. Holte and K.A. Scheidt, Nat. Chem., 2, 766 (2010);https://doi.org/10.1038/nchem.727
- A.G. Kravina, J. Mahatthananchai and J.W. Bode, Angew. Chem. Int. Ed., 51, 9433 (2012);https://doi.org/10.1002/anie.201204145
- B. Zhang, P. Feng, L.-H. Sun, Y. Cui, S. Ye and N. Jiao, Chem. Eur. J., 18, 9198 (2012);https://doi.org/10.1002/chem.201201375
- V. Nair, B.P. Babu, S. Vellalath and E. Suresh, Chem. Commun., 747 (2008);https://doi.org/10.1039/B715733A
- C. Guo, M. Schedler, C.G. Daniliuc and F. Glorius, Angew. Chem. Int. Ed., 53, 10232 (2014);https://doi.org/10.1002/anie.201405381
- M. Wang, Z.Q. Rong and Y. Zhao, Chem. Commun., 50, 15309 (2014);https://doi.org/10.1039/C4CC07788A
- A. Patra, A. Bhunia, S.R. Yetra, R.G. Gonnade and A.T. Biju, Org. Chem. Front., 2, 1584 (2015);https://doi.org/10.1039/C5QO00242G
- V. Nair, S. Vellalath, M. Poonoth and E. Suresh, J. Am. Chem. Soc., 128, 8736 (2006);https://doi.org/10.1021/ja0625677
- V. Nair, R.R. Paul, D.V.M. Padmaja, N. Aiswarya, C.R. Sinu and A. Jose, Tetrahedron, 67, 9885 (2011);https://doi.org/10.1016/j.tet.2011.09.113
- V. Nair, C. Sinu, D. Padmaja, P. Jini and K. Lakshmi, Synlett, 24, 1671 (2013);https://doi.org/10.1055/s-0033-1339308
- K.C. Seetha Lakshmi, J. Krishnan, C.R. Sinu, S. Varughese and V. Nair, Org. Lett., 16, 6374 (2014);https://doi.org/10.1021/ol5031684
- W.W.Y. Leong, X. Chen and Y.R. Chi, Green Chem., 15, 1505 (2013);https://doi.org/10.1039/c3gc40397a
- V. Nair, C.R. Sinu, B.P. Babu, V. Varghese, A. Jose and E. Suresh, Org. Lett., 11, 5570 (2009);https://doi.org/10.1021/ol901918x
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- T. Tsujihara, K. Takenaka, K. Onitsuka, M. Hatanaka and H. Sasai, J. Am. Chem. Soc., 131, 3452 (2009);https://doi.org/10.1021/ja809965e
- K. Takenaka, S.C. Mohanta and H. Sasai, Angew. Chem. Int. Ed., 53, 4675 (2014);https://doi.org/10.1002/anie.201311172
- K. Takenaka, J. Synth. Org. Chem. Jpn., 73, 964 (2015);https://doi.org/10.5059/yukigoseikyokaishi.73.964
- D.H. Dethe and V. Kumar B, Org. Chem. Front., 2, 548 (2015);https://doi.org/10.1039/C5QO00030K
- R.J. Sharpe and J.S. Johnson, J. Org. Chem., 80, 9740 (2015);https://doi.org/10.1021/acs.joc.5b01844
- S.-S. Gao, X.-M. Li, K. Williams, P. Proksch, N.-Y. Ji and B.-G. Wang, J. Nat. Prod., 79, 2066 (2016);https://doi.org/10.1021/acs.jnatprod.6b00403
- D.T. George, E.J. Kuenstner and S.V. Pronin, Synlett, 28, 12 (2017);https://doi.org/10.1055/s-0036-1588669
- M.A. Abozeid, S. Sairenji, S. Takizawa, M. Fujita and H. Sasai, Chem. Commun., 53, 6887 (2017);https://doi.org/10.1039/C7CC03199H
- A. Gopalsamy, M. Shi, G. Ciszewski, K. Park, J.W. Ellingboe, M. Orlowski, B. Feld and A.Y.M. Howe, Bioorg. Med. Chem. Lett., 16, 2532 (2006);https://doi.org/10.1016/j.bmcl.2006.01.105
- Z. Wang, X. Xu, Z. Gu, W. Feng, H. Qian, Z. Li, X. Sun and O. Kwon, Chem. Commun., 52, 2811 (2016);https://doi.org/10.1039/C5CC08596A
- Y. Wang, H. Lu and P.-F. Xu, Acc. Chem. Res., 48, 1832 (2015);https://doi.org/10.1021/acs.accounts.5b00217
- L. Tian, Y.-C. Luo, X.-Q. Hu and P.-F. Xu, Asian J. Org. Chem., 5, 580 (2016);https://doi.org/10.1002/ajoc.201500486
- M. Benadallah, O. Talhi, F. Nouali, N. Choukchou-Braham, K. Bachari and A.M.S. Silva, Curr. Med. Chem., 25, 3748 (2018);https://doi.org/10.2174/0929867325666180309124821
- X. Xie, W. Huang, C. Peng and B. Han, Adv. Synth. Catal., 360, 194 (2018);https://doi.org/10.1002/adsc.201700927
- S. Kotha, N.R. Panguluri and R. Ali, Eur. J. Org. Chem., 36, 5316 (2017);https://doi.org/10.1002/ejoc.201700439
- R.B. Van Order and H.G. Lindwall, Chem. Rev., 30, 69 (1942);https://doi.org/10.1021/cr60095a004
- E. Fischer and F. Jourdan, Chem. Ber., 16, 2241 (1883);https://doi.org/10.1002/cber.188301602141
- N. Dharmasiri, S. Dharmasiri and M. Estelle, Nature, 435, 441 (2005);https://doi.org/10.1038/nature03543
- S. Kepinski and O. Leyser, Nature, 435, 446 (2005);https://doi.org/10.1038/nature03542
- K. Mockaitis and M. Estelle, Annu. Rev. Cell Dev. Biol., 24, 55 (2008);https://doi.org/10.1146/annurev.cellbio.23.090506.123214
- G.F.E. Scherer, J. Exp. Bot., 62, 3339 (2011);https://doi.org/10.1093/jxb/err033
- T.P. Singh, O.M. Singh, N. Kaur, M. Sanduja, G. Singh, P.M.S. Bedi and S. Sharma, Mini Rev. Med. Chem., 18, 837 (2018);https://doi.org/10.2174/1389557517666170807124507
- D.H. Dethe, S. Das, V.B. Kumar and N.A. Mir, Chem. Eur. J., 24, 8980 (2018);https://doi.org/10.1002/chem.201800970
- S. Sahu, S. Beauty and M.S. Maji, Org. Lett., 20, 6485 (2018);https://doi.org/10.1021/acs.orglett.8b02804
- J.-L. Wu, C.-S. Wang, J.-R. Wang, G.-J. Mei and F. Shi, Org. Biomol. Chem., 16, 5457 (2018);https://doi.org/10.1039/C8OB01427B
- D.L. Hughes, Org. Prep. Proced. Int., 25, 607 (1993);https://doi.org/10.1080/00304949309356257
- G.R. Humphrey and J.T. Kuethe, Chem. Rev., 106, 2875 (2006);https://doi.org/10.1021/cr0505270
- M.G. Ciulla, S. Zimmermann and K. Kumar, Org. Biomol. Chem., 17, 413 (2019);https://doi.org/10.1039/C8OB02620C
- CCDC 1966911 (3a) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from Data Centre via www.ccdc.cam.ac.uk/data_request/cif.
References
V. Nair, S. Bindu and V. Sreekumar, Angew. Chem. Int. Ed., 43, 5130 (2004);https://doi.org/10.1002/anie.200301714
V. Nair, S. Vellalath and B.P. Babu, Chem. Soc. Rev., 37, 2691 (2008);https://doi.org/10.1039/b719083m
J.L. Moore and T. Rovis, Top. Curr. Chem., 291, 77 (2009);https://doi.org/10.1007/128_2008_18
V. Nair, R.S. Menon, A.T. Biju, C.R. Sinu, R.R. Paul, A. Jose and V. Sreekumar, Chem. Soc. Rev., 40, 5336 (2011);https://doi.org/10.1039/c1cs15139h
X. Bugaut and F. Glorius, Chem. Soc. Rev., 41, 3511 (2012);https://doi.org/10.1039/c2cs15333e
R.S. Menon, A.T. Biju and V. Nair, Chem. Soc. Rev., 44, 5040 (2015);https://doi.org/10.1039/C5CS00162E
D.M. Flanigan, F. Romanov-Michailidis, N.A. White and T. Rovis, Chem. Rev., 115, 9307 (2015);https://doi.org/10.1021/acs.chemrev.5b00060
M.H. Wang and K.A. Scheidt, Angew. Chem. Int. Ed., 55, 14912 (2016);https://doi.org/10.1002/anie.201605319
R.S. Menon, A.T. Biju and V. Nair, Beilstein J. Org. Chem., 12, 444 (2016);https://doi.org/10.3762/bjoc.12.47
K. Zeitler, Angew. Chem. Int. Ed., 44, 7506 (2005);https://doi.org/10.1002/anie.200502617
A. Grossmann and D. Enders, Angew. Chem. Int. Ed., 51, 314 (2012);https://doi.org/10.1002/anie.201105415
S.J. Ryan, L. Candish and D.W. Lupton, Chem. Soc. Rev., 42, 4906 (2013);https://doi.org/10.1039/c3cs35522e
X.-Y. Chen and S. Ye, Org. Biomol. Chem., 11, 7991 (2013);https://doi.org/10.1039/c3ob41469h
S. Ye and X.-Y. Chen, Synlett, 24, 1614 (2013);https://doi.org/10.1055/s-0033-1339300
M.N. Hopkinson, C. Richter, M. Schedler and F. Glorius, Nature, 510, 485 (2014);https://doi.org/10.1038/nature13384
A. Nickon and J.L. Lambert, J. Am. Chem. Soc., 84, 4604 (1962);https://doi.org/10.1021/ja00882a055
E. Nakamura and I. Kuwajima, J. Am. Chem. Soc., 99, 7360 (1977);https://doi.org/10.1021/ja00464a048
S. De Lombaert, B. Lesur and L. Ghosez, Tetrahedron Lett., 23, 4251 (1982);https://doi.org/10.1016/S0040-4039(00)88717-1
M.R. Binns and R.K. Haynes, J. Org. Chem., 46, 3790 (1981);https://doi.org/10.1021/jo00332a005
S.E. Schaus, J. Branalt and E.N. Jacobsen, J. Org. Chem., 63, 403 (1998);https://doi.org/10.1021/jo971758c
H. Ahlbrecht, G. Bonnet, D. Enders and M. Zimmermann, Tetrahedron Lett., 21, 3175 (1980);https://doi.org/10.1016/S0040-4039(00)77438-7
S.S. Sohn, E.L. Rosen and J.W. Bode, J. Am. Chem. Soc., 126, 14370 (2004);https://doi.org/10.1021/ja044714b
C. Burstein and F. Glorius, Angew. Chem. Int. Ed., 43, 6205 (2004);https://doi.org/10.1002/anie.200461572
I. Kuwajima and E. Nakamura, eds.: B.M. Trost and I. Fleming, Compre-hensive Organic Synthesis, Pergamon, New York, vol. 2, p. 441 (1991).
V.J. Lee, eds.: B.M. Trost and I. Fleming, Comprehensive Organic Synthesis, Pergamon: New York, vol. 4, p. 117 (1991).
V. Nair, M. Poonoth, S. Vellalath, E. Suresh and R. Thirumalai, J. Org. Chem., 71, 8964 (2006);https://doi.org/10.1021/jo0615706
Z. Wu, X. Wang, F. Li, J. Wu and J. Wang, Org. Lett., 17, 3588 (2015);https://doi.org/10.1021/acs.orglett.5b01692
A. Chan and K.A. Scheidt, J. Am. Chem. Soc., 130, 2740 (2008);https://doi.org/10.1021/ja711130p
V. Nair, V. Varghese, B.P. Babu, C.R. Sinu and E. Suresh, Org. Biomol. Chem., 8, 761 (2010);https://doi.org/10.1039/b922981g
M. He and J.W. Bode, Org. Lett., 7, 3131 (2005);https://doi.org/10.1021/ol051234w
D.E.A. Raup, B. Cardinal-David, D. Holte and K.A. Scheidt, Nat. Chem., 2, 766 (2010);https://doi.org/10.1038/nchem.727
A.G. Kravina, J. Mahatthananchai and J.W. Bode, Angew. Chem. Int. Ed., 51, 9433 (2012);https://doi.org/10.1002/anie.201204145
B. Zhang, P. Feng, L.-H. Sun, Y. Cui, S. Ye and N. Jiao, Chem. Eur. J., 18, 9198 (2012);https://doi.org/10.1002/chem.201201375
V. Nair, B.P. Babu, S. Vellalath and E. Suresh, Chem. Commun., 747 (2008);https://doi.org/10.1039/B715733A
C. Guo, M. Schedler, C.G. Daniliuc and F. Glorius, Angew. Chem. Int. Ed., 53, 10232 (2014);https://doi.org/10.1002/anie.201405381
M. Wang, Z.Q. Rong and Y. Zhao, Chem. Commun., 50, 15309 (2014);https://doi.org/10.1039/C4CC07788A
A. Patra, A. Bhunia, S.R. Yetra, R.G. Gonnade and A.T. Biju, Org. Chem. Front., 2, 1584 (2015);https://doi.org/10.1039/C5QO00242G
V. Nair, S. Vellalath, M. Poonoth and E. Suresh, J. Am. Chem. Soc., 128, 8736 (2006);https://doi.org/10.1021/ja0625677
V. Nair, R.R. Paul, D.V.M. Padmaja, N. Aiswarya, C.R. Sinu and A. Jose, Tetrahedron, 67, 9885 (2011);https://doi.org/10.1016/j.tet.2011.09.113
V. Nair, C. Sinu, D. Padmaja, P. Jini and K. Lakshmi, Synlett, 24, 1671 (2013);https://doi.org/10.1055/s-0033-1339308
K.C. Seetha Lakshmi, J. Krishnan, C.R. Sinu, S. Varughese and V. Nair, Org. Lett., 16, 6374 (2014);https://doi.org/10.1021/ol5031684
W.W.Y. Leong, X. Chen and Y.R. Chi, Green Chem., 15, 1505 (2013);https://doi.org/10.1039/c3gc40397a
V. Nair, C.R. Sinu, B.P. Babu, V. Varghese, A. Jose and E. Suresh, Org. Lett., 11, 5570 (2009);https://doi.org/10.1021/ol901918x
G.B. Bajracharya, M.A. Arai, P.S. Koranne, T. Suzuki, S. Takizawa and H. Sasai, Bull. Chem. Soc. Jpn., 82, 285 (2009);https://doi.org/10.1246/bcsj.82.285
T. Tsujihara, K. Takenaka, K. Onitsuka, M. Hatanaka and H. Sasai, J. Am. Chem. Soc., 131, 3452 (2009);https://doi.org/10.1021/ja809965e
K. Takenaka, S.C. Mohanta and H. Sasai, Angew. Chem. Int. Ed., 53, 4675 (2014);https://doi.org/10.1002/anie.201311172
K. Takenaka, J. Synth. Org. Chem. Jpn., 73, 964 (2015);https://doi.org/10.5059/yukigoseikyokaishi.73.964
D.H. Dethe and V. Kumar B, Org. Chem. Front., 2, 548 (2015);https://doi.org/10.1039/C5QO00030K
R.J. Sharpe and J.S. Johnson, J. Org. Chem., 80, 9740 (2015);https://doi.org/10.1021/acs.joc.5b01844
S.-S. Gao, X.-M. Li, K. Williams, P. Proksch, N.-Y. Ji and B.-G. Wang, J. Nat. Prod., 79, 2066 (2016);https://doi.org/10.1021/acs.jnatprod.6b00403
D.T. George, E.J. Kuenstner and S.V. Pronin, Synlett, 28, 12 (2017);https://doi.org/10.1055/s-0036-1588669
M.A. Abozeid, S. Sairenji, S. Takizawa, M. Fujita and H. Sasai, Chem. Commun., 53, 6887 (2017);https://doi.org/10.1039/C7CC03199H
A. Gopalsamy, M. Shi, G. Ciszewski, K. Park, J.W. Ellingboe, M. Orlowski, B. Feld and A.Y.M. Howe, Bioorg. Med. Chem. Lett., 16, 2532 (2006);https://doi.org/10.1016/j.bmcl.2006.01.105
Z. Wang, X. Xu, Z. Gu, W. Feng, H. Qian, Z. Li, X. Sun and O. Kwon, Chem. Commun., 52, 2811 (2016);https://doi.org/10.1039/C5CC08596A
Y. Wang, H. Lu and P.-F. Xu, Acc. Chem. Res., 48, 1832 (2015);https://doi.org/10.1021/acs.accounts.5b00217
L. Tian, Y.-C. Luo, X.-Q. Hu and P.-F. Xu, Asian J. Org. Chem., 5, 580 (2016);https://doi.org/10.1002/ajoc.201500486
M. Benadallah, O. Talhi, F. Nouali, N. Choukchou-Braham, K. Bachari and A.M.S. Silva, Curr. Med. Chem., 25, 3748 (2018);https://doi.org/10.2174/0929867325666180309124821
X. Xie, W. Huang, C. Peng and B. Han, Adv. Synth. Catal., 360, 194 (2018);https://doi.org/10.1002/adsc.201700927
S. Kotha, N.R. Panguluri and R. Ali, Eur. J. Org. Chem., 36, 5316 (2017);https://doi.org/10.1002/ejoc.201700439
R.B. Van Order and H.G. Lindwall, Chem. Rev., 30, 69 (1942);https://doi.org/10.1021/cr60095a004
E. Fischer and F. Jourdan, Chem. Ber., 16, 2241 (1883);https://doi.org/10.1002/cber.188301602141
N. Dharmasiri, S. Dharmasiri and M. Estelle, Nature, 435, 441 (2005);https://doi.org/10.1038/nature03543
S. Kepinski and O. Leyser, Nature, 435, 446 (2005);https://doi.org/10.1038/nature03542
K. Mockaitis and M. Estelle, Annu. Rev. Cell Dev. Biol., 24, 55 (2008);https://doi.org/10.1146/annurev.cellbio.23.090506.123214
G.F.E. Scherer, J. Exp. Bot., 62, 3339 (2011);https://doi.org/10.1093/jxb/err033
T.P. Singh, O.M. Singh, N. Kaur, M. Sanduja, G. Singh, P.M.S. Bedi and S. Sharma, Mini Rev. Med. Chem., 18, 837 (2018);https://doi.org/10.2174/1389557517666170807124507
D.H. Dethe, S. Das, V.B. Kumar and N.A. Mir, Chem. Eur. J., 24, 8980 (2018);https://doi.org/10.1002/chem.201800970
S. Sahu, S. Beauty and M.S. Maji, Org. Lett., 20, 6485 (2018);https://doi.org/10.1021/acs.orglett.8b02804
J.-L. Wu, C.-S. Wang, J.-R. Wang, G.-J. Mei and F. Shi, Org. Biomol. Chem., 16, 5457 (2018);https://doi.org/10.1039/C8OB01427B
D.L. Hughes, Org. Prep. Proced. Int., 25, 607 (1993);https://doi.org/10.1080/00304949309356257
G.R. Humphrey and J.T. Kuethe, Chem. Rev., 106, 2875 (2006);https://doi.org/10.1021/cr0505270
M.G. Ciulla, S. Zimmermann and K. Kumar, Org. Biomol. Chem., 17, 413 (2019);https://doi.org/10.1039/C8OB02620C
CCDC 1966911 (3a) contains the supplementary crystallographic data for this paper. These data can be obtained free of charge from Data Centre via www.ccdc.cam.ac.uk/data_request/cif.