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Letters in Organic Chemistry

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

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Letter Article

Metal Free Simple and Efficient Synthesis of Tetrahydropyrrolo[1,2-a]- Pyrazine Based on a Cascade Strategy

Author(s): Chakrapani Sanaboina, Samir Kumar Mandal* and Samaresh Jana*

Volume 20, Issue 10, 2023

Published on: 18 May, 2023

Page: [916 - 921] Pages: 6

DOI: 10.2174/1570178620666230327114033

Price: $65

Abstract

A simple and efficient synthesis of pyrrolo[1,2-a]pyrazine using Schiff base formation, intramolecular cyclization (or N-alkylation), and Pictet–Spengler type reaction (hetero-aromatisation) has been developed. In this chemistry, metal-free, cost and time-effective processes have been highlighted to afford the complex nitrogenous scaffold using simple starting materials.

Keywords: Pyrrolyl-ethanamine, halo-aldehyde, Pyrrolo[1, 2-a]pyrazines, cascade reaction, Pictet-Spengler reaction, heteroaromatization.

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[1]
(a) Poullennec, K.G.; Kelly, A.T.; Romo, D. Org. Lett., 2002, 4(16), 2645-2648.
[http://dx.doi.org/10.1021/ol026140q] [PMID: 12153199];
(b) Sharma, G.; Magdoff-Fairchild, B. J. Org. Chem., 1977, 42(25), 4118-4124.
[http://dx.doi.org/10.1021/jo00445a028];
(c) Han, S.; Siegel, D.S.; Morrison, K.C.; Hergenrother, P.J.; Movassaghi, M. J. Org. Chem., 2013, 78(23), 11970-11984.
[http://dx.doi.org/10.1021/jo4020112] [PMID: 24152243];
(d) Negoro, T.; Murata, M.; Ueda, S.; Fujitani, B.; Ono, Y.; Kuromiya, A.; Komiya, M.; Suzuki, K.; Matsumoto, J. J. Med. Chem., 1998, 41(21), 4118-4129.
[http://dx.doi.org/10.1021/jm9802968] [PMID: 9767647];
(e) Kiran, G.S.; Priyadharsini, S.; Sajayan, A.; Ravindran, A. RSC Advances, 2018, 8, 17837-17846.
[http://dx.doi.org/10.1039/C8RA00820E] [PMID: 35542054]
[2]
(a) Lucca, G.V.D.; Otto, M.J. Bioorg. Med. Chem. Lett., 1992, 2, 1639-1644.
[http://dx.doi.org/10.1016/S0960-894X(00)80447-3];
(b) Wenzel, B.; Mollitor, J.; Deuther-Conrad, W.; Dukic-Stefanovic, S.; Kranz, M.; Vraka, C.; Teodoro, R.; Günther, R.; Donat, C.K.; Ludwig, F.A.; Fischer, S.; Smits, R.; Wadsak, W.; Mitterhauser, M.; Steinbach, J.; Hoepping, A.; Brust, P. J. Med. Chem., 2016, 59(5), 1800-1817.
[http://dx.doi.org/10.1021/acs.jmedchem.5b01080] [PMID: 26796795]
[3]
(a) Peresada, V.P.; Medvedev, O.S.; Likhosherstov, A.M.; Skoldinov, A.P. >Khim.-. Farm. Zh., 1987, 21, 1054.;
(b) Chem. Abstr., 1988, 108, 68298g.
[4]
Likhosherstov, A.M.; Filippova, O.V.; Peresada, V.P. Pharm. Chem. J., 2003, 37(1), 6-9.
[http://dx.doi.org/10.1023/A:1023634625558]
[5]
(a) Seredenin, S.B.; Voronina, T.A.; Beshimov, A.; Peresada, V.P.; Likhosherstov, A.M. RU 2099055. 1997.;
(b) Chem. Abstr., 1998, 128, 290245j.
[6]
Yang, S.; Lu, D.; Ouyang, P. Bioorg. Med. Chem. Lett., 2018, 28(17), 3004-3008.
[http://dx.doi.org/10.1016/j.bmcl.2018.05.019] [PMID: 30061030]
[7]
Seredenin, S.B.; Voronina, T.A.; Likhosherstov, A.M.; Peresada, V.P.; Molodavkin, G.M.; Halikas, J.A.U.S. US5378846A 1995.
[8]
(a) Peresada, V.P.; Medvedev, O.S.; Likhosherstov, A.M.; Skoldinov, A.P. Pharm. Chem. J., 1987, 21(9), 619-624.;
(b) Henrik, M.; Weil, T.; Müller, S.; Nagel, J.; Kauss, V.; Zemribo, R.; Erdmare, E. WO 2009095254. 2009.;
(c) Chem. Abstr., 2009, 151, 245654.
[9]
(a) Zhu, B.; Marinelli, B.A.; Goldschmidt, R.; Foleno, B.D.; Hilliard, J.J.; Bush, K.; Macielag, M.J. Bioorg. Med. Chem. Lett., 2009, 19(17), 4933-4936.
[http://dx.doi.org/10.1016/j.bmcl.2009.07.087] [PMID: 19646867];
(b) Ambrosio, M.; Guerriero, A.; Debitus, C.; Ribes, O.; Pusset, J.; Leroy, S.; Pietra, F. J. Chem. Soc. Chem. Commun., 1993, 16, 1305-1306.
[http://dx.doi.org/10.1039/c39930001305]
[10]
Zhang, H.J.; Yang, Z.P.; Gu, Q.; You, S.L. Org. Lett., 2019, 21(9), 3314-3318.
[http://dx.doi.org/10.1021/acs.orglett.9b01060] [PMID: 31001983]
[11]
(a) Huang, W.X.; Yu, C.B.; Shi, L.; Zhou, Y.G. Org. Lett., 2014, 16(12), 3324-3327.
[http://dx.doi.org/10.1021/ol5013313] [PMID: 24911796];
(b) Shu-Boa, H.; Mu-Wang, C.; Xiao-Yong, Z.; Yong-Gui, Z. Acta Chimi. Sin., 2018, 76, 103-106.
[http://dx.doi.org/10.6023/A17110476];
(c) Skoldinov, A. P.; Likhosherstov, A. M.; Peresada, V. P. DE 2832488 1980.;
(d) Skoldinov, A. P.; Likhosherstov, A. M.; Peresada, V. P. GB2025936A, 1980.;
(e) Skoldinov, A. P.; Likhosherstov, A. M.; Peresada, V. P. SU 798104, 1981.;
(f) Markus, H.; Tanja, W.; Sibylle, M.; Jens, N.; Andreas, G.; Valerjans, K.; Ronalds, Z.; Elina, E. WO 2009095254 2009.;
(g) Gualandi, A.; Cerisoli, L.; Monari, M.; Savoia, D. Synthesis, 2011, 909-918.;
(h) Ghandi, M.; Salah, S.; Taheri, A.; Abbasi, A. Mol. Divers.,, 2018, 22(2), 291-303.
[http://dx.doi.org/10.1007/s11030-017-9801-4] [PMID: 29230611];
(i) He, Y.; Lin, M..; Li, Z.; Liang, X.; Li, G.; Antilla, J.C. Org. Lett., 2011, 13(17), 4490-4493.
[http://dx.doi.org/10.1021/ol2018328] [PMID: 21834569];
(j) Basceken, S.; Balci, M. J. Org. Chem., 2015, 80(8), 3806-3814.
[http://dx.doi.org/10.1021/acs.joc.5b00034] [PMID: 25790184]
[12]
Chithanna, S.; Yang, D.Y. J. Org. Chem., 2019, 84(3), 1339-1347.
[http://dx.doi.org/10.1021/acs.joc.8b02819] [PMID: 30604610]
[13]
Sanaboina, C.; Jana, S.; Chidara, S.; Patro, B.; Raolji, G.B.; Eppakayala, L. Tetrahedron Lett., 2012, 53(37), 5027-5029.
[http://dx.doi.org/10.1016/j.tetlet.2012.07.044]

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