R. R. Wani, H. K. Chaudhari, and B. S. Takale
Vol 000
51, 7843; (e) He, X. Y.; Zou, P.; Qiu, J.; Hou, L.; Jiang, S.; Liu, S.; Xie, L.
Bioorg Med Chem 2011, 19, 6726.
All products are known compounds and were identified by their melting
point, 1H NMR spectra according to the literature. For example, 2a; White
solid, Mp 59–60°C, 1H NMR (400 MHz, CDCl3) δ 7.50–7.38 (m, 4H),
7.28–7.25 (m, 1H), 7.13–7.10 (m, 2H), 6.47–6.29 (m, 2H); 13C NMR
(75MHz, CDCl3): δ = 140.74, 129.51, 125.59, 120.51, 119.29, 110.35;
C10H9N; MS m/z143 (M+) 2e; Yellow Solid, Mp 43–46°C, 1H NMR,
(400 MHz, CDCl3) δ 8.14 (d, J = 36.8 Hz, 1H), 7.30 (d, J = 47.5 Hz,
2H), 6.83 (d, J = 1.9 Hz, 2H), 6.37 (d, J = 1.9 Hz, 2H), 2.38 (s, 3H);
13C NMR (75 MHz, CDCl3): δ = 146.12, 145.70, 134.46, 126.79,
126.58, 122.07, 121.72, 110.24, 77.34, 76.71, 18.63; C11H1N2O2, MS
m/z 202(M+).
[11] Ferenc, F.; Szilvia, D.; Zoltán, M.; Tamás, H.; László, B.;
Boros, S.; Barbara, B.; Tamás, H.; Miklós, N.; Béla, M. Tetrahedron
2016, 72, 5444.
[12] Gilow, H. M.; Edward Burton, D. J Org Chem 1981, 46, 2221.
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Pays-Bas 1943, 6, 177; (b) Varvounis, K. J Heterocyclic Chem 1996, 33,
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[2] For original reactions, see (a) Paal, C. Ber 1884, 17, 2756; (b)
Knorr, L. Ber 1885, 17, 2863; (c) Paal, C. Ber 1885, 18, 367.
[3] For recent way of synthesis of N-substituted pyrroles, see;
Andreou, D.; Kallitsakis, M. G.; Loukopoulos, E.; Gabriel, C.; Kostakis,
G. E.; Lykakis, I. N J Org Chem 2018, 83, 2104.
[4] Khaghaninejad, S.; Heravi, M. M. Adv Heterocycl Chem,
Chapter-3 2014, 111, 95.
[5] Thayer, A. M. Chem Eng News 2013, 91, 10.
[6] Chaudhari, H. K.; Pahelkar, A.; Takale, B. S. Tetrahedron Lett
2017, 58, 4107.
[7] (a) Clauson-Kaas, N.; Tyle, Z. Acta Chem Scand 1952, 6,
667; (b) Elming, N.; Clauson-Kaas, N. Acta Chem Scand 1952, 6,
867.
[8] Satyanarayan, V. S. V.; Sivakumar, A. Ultrason Sonochem
2011, 18, 917.
[9] Banik, B. K.; Banik, I.; Renteria, M.; Dasgupt, S. K. Tetrahe-
dron Lett 2005, 46, 2643.
[14] Ewen, J. A.; Elder, M. J.; Jones, R. L.; Rheingold, A. L.;
Liable-Sands, L. M.; Sommer, R. D. J Am Chem Soc 2001, 123, 4763.
[10] For Experimental procedure and characterization data of se-
lected compounds, follow; General procedure for the synthesis of N-
Substituted Pyrroles: To the reaction mixture of primary amines (2 mmol)
and 2, 5-dimethoxy tetrahydrofuran (1.5 equiv.) was added calcium nitrate
(40 mol%). The reaction was stirred at reflux (100 oC). The progress of the
reaction was monitored by TLC. After completion of reaction 10 mL ethyl
acetate added. The reaction mixture is filtered, and filtrate was evaporated
using rota evaporator under vacuum to get crude product. Crude product is
purified by column chromatography using silica as stationary phase and
hexane: ethyl acetate (10:0 to 8:2) as mobile phase to afford pure product.
SUPPORTING INFORMATION
Additional supporting information may be found online
in the Supporting Information section at the end of the
article.
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet