A. Rammohan, G. Mallikarjuna Reddy, J. Raul Garcia, G. V. Zyryanov, G. Sravya,
N. Bakthavatchala Reddy, and G. Yuvaraja
Vol 000
9.28 (s, 1H, HC=N) ppm. 13C NMR (75 MHz, CDCl3):
δ = 163.0, 160.8, 142.9, 132.7, 130.0, 129.8, 128.9,
128.2, 127.4, 127.1, 120.3 ppm. HRMS: m/z Calcd for
C17H11FN2O2 (M + H)+ 295.0883; Found 295.0881.
(E)-1-(4-((4-Chlorobenzylidene)amino)phenyl)-1H-pyrrole-
(E)-1-(4-((2-Bromobenzylidene)amino)phenyl)-1H-pyrrole-
1
2,5-dione (5j).
Light yellow solid. mp 177–179°C. H
NMR (300 MHz, CDCl3): δ = 7.03–7.59 (m, 10H, Ar-H),
9.13 (s, 1H, HC=N) ppm. 13C NMR (75 MHz, CDCl3):
δ = 164.7, 156.9, 148.0, 145.7, 142.6, 134.8, 130.6, 129.9,
128.3, 120.2, 117.4, 105.9, 102.7 ppm. HRMS: m/z Calcd
for C17H11BrN2O2 (M + H)+ 355.0082; Found 355.0081.
1
2,5-dione (5c). Light yellow solid. mp 187–189°C. H
NMR (300 MHz, CDCl3): δ = 7.00–7.57 (m, 10H, Ar-H),
9.30 (s, 1H, HC=N) ppm. 13C NMR (75 MHz, CDCl3):
δ = 165.3, 160.7, 141.7, 137.5, 131.6, 129.9, 128.3,
127.4, 125.1, 123.6, 120.8 ppm. HRMS: m/z Calcd for
C17H11ClN2O2 (M + H)+ 311.0587; Found 311.0584.
(E)-1-(4-((4-Bromobenzylidene)amino)phenyl)-1H-pyrrole-
(E)-1-(4-((2-Fluorobenzylidene)amino)phenyl)-1H-pyrrole-
1
2,5-dione (5k).
Light yellow solid. mp 148–150°C. H
NMR (300 MHz, CDCl3): δ = 7.19–7.88 (m, 10H, Ar-H),
9.29 (s, 1H, HC=N) ppm. 13C NMR (75 MHz, CDCl3):
δ = 163.5, 161.5, 143.5, 137.6, 136.4, 131.0, 127.6, 126.3,
120.5, 120.2, 119.4, 118.0, 117.7 ppm. HRMS: m/z Calcd
for C17H11FN2O2 (M + H)+ 295.0883; Found 295.0878.
1
2,5-dione (5d). Light yellow solid. mp 164–166°C. H
NMR (300 MHz, CDCl3): δ = 6.97–7.50 (m, 10H, Ar-H),
9.09 (s, 1H, HC=N) ppm. 13C NMR (75 MHz, CDCl3):
δ = 163.6, 161.6, 141.7, 136.0, 131.1, 127.8, 126.2,
119.8, 118.7, 118.1, 117.9 ppm. HRMS: m/z Calcd for
C17H11BlN2O2 (M + H)+ 355.0082; Found 355.0079.
(E)-1-(4-((4-Hydroxybenzylidene)amino)phenyl)-1H-pyrrole-
(E)-1-(4-((3-Chlorobenzylidene)amino)phenyl)-1H-pyrrole-
1
2,5-dione (5l).
Light yellow solid. mp 121–123°C. H
NMR (300 MHz, CDCl3): δ = 7.15–7.62 (m, 10H, Ar-H),
9.10 (s, 1H, HC=N) ppm. 13C NMR (75 MHz, CDCl3):
δ = 164.7, 158.2, 142.8, 137.6, 136.4, 133.8, 133.2, 132.2,
129.5, 128.6, 125.1, 123.2, 119.9 ppm. HRMS: m/z Calcd
for C17H11ClN2O2 (M + H)+ 311.0587; Found 295.0585.
(E)-1-(4-((2-Aminobenzylidene)amino)phenyl)-1H-pyrrole-
1
2,5-dione (5e). Light yellow solid. mp 142–145°C. H
NMR (300 MHz, CDCl3): δ = 7.08–7.59 (m, 10H, Ar-H),
9.07 (s, 1H, HC=N) ppm. 13C NMR (75 MHz, CDCl3):
δ = 164.7, 160.7, 140.9, 135.2, 130.6, 130.5, 128.6,
120.1, 115.4, 115.3, 105.5 ppm. HRMS: m/z Calcd for
C17H12N2O3 (M + H)+ 293.0926; Found 293.0921.
1
2,5-dione (5m). Light yellow solid. mp 183–185°C. H
NMR (300 MHz, CDCl3): δ = 6.93–7.49 (m, 10H, Ar-
H), 9.05 (s, 1H, HC=N) ppm. 13C NMR (75 MHz,
CDCl3): δ = 165.8, 163.6, 144.8, 135.1, 130.5, 130.2,
129.9, 128.8, 127.2, 127.0, 124.2, 122.5, 120.6 ppm.
HRMS: m/z Calcd for C17H13N3O2 (M + H)+ 292.1086;
(E)-1-(4-((4-Nitrobenzylidene)amino)phenyl)-1H-pyrrole-
1
2,5-dione (5f).
Light yellow solid. mp 127–129°C. H
NMR (300 MHz, CDCl3): δ = 7.06–8.05 (m, 10H, Ar-H),
9.28 (s, 1H, HC=N) ppm. 13C NMR (75 MHz, CDCl3):
δ = 164.8, 162.8, 140.6, 136.8, 130.8, 128.9, 128.4,
Found 292.1085.
(E)-1-(4-((4-Iodobenzylidene)amino)phenyl)-1H-pyrrole-2,5-
dione (5n). Light yellow solid. mp 171–173°C. 1H NMR
127.4, 127.2, 125.6, 125.3 ppm. HRMS: m/z Calcd for
C17H11N3O4 (M + H)+ 322.0828; Found 322.0827.
(E)-1-(4-((4-Methylbenzylidene)amino)phenyl)-1H-pyrrole-
(300 MHz, CDCl3): δ = 7.20–7.98 (m, 10H, Ar-H), 9.14 (s,
1H, HC=N) ppm. 13C NMR (75 MHz, CDCl3): δ = 163.4,
160.8, 143.9, 142.4, 131.9, 128.7, 127.0, 124.5, 121.4,
120.0, 115.0 ppm. HRMS: m/z Calcd for C17H11IN2O2
(M + H)+ 402.9943; Found 402.9941.
1
2,5-dione (5g). Light yellow solid. mp 130–132°C. H
NMR (300 MHz, CDCl3): δ = 3.49 (S, 3H, CH3), 6.95–
7.50 (m, 10H, Ar-H), 9.16 (s, 1H, HC=N) ppm. 13C
NMR (75 MHz, CDCl3): δ = 162.8, 160.9, 141.7, 136.5,
132.0, 129.2, 127.3, 124.8, 123.0, 120.2, 117.1,
38.4 ppm. HRMS: m/z Calcd for C18H14N2O2 (M + H)+
(E)-1-(4-((2-Iodobenzylidene)amino)phenyl)-1H-pyrrole-2,5-
dione (5o). Light yellow solid. mp 211–213°C. 1H NMR
(300 MHz, CDCl3): δ = 7.25–7.87 (m, 10H, Ar-H), 9.10 (s,
1H, HC=N) ppm. 13C NMR (75 MHz, CDCl3): δ = 165.4,
160.9, 141.3, 140.3, 136.9, 133.4, 131.5, 130.2, 128.6,
128.5, 120.0, 115.7, 155.5 ppm. HRMS: m/z Calcd for
C17H11IN2O2 (M + H)+ 402.9943; Found 402.9940.
291.1134; Found 291.1131.
(E)-1-(4-((4-Methoxybenzylidene)amino)phenyl)-1H-pyrrole-
1
2,5-dione (5h). Light yellow solid. mp 159–161°C. H
NMR (300 MHz, CDCl3): δ = 3.87 (S, 3H, OCH3), 6.88–
7.30 (m, 10H, Ar-H), 9.11 (s, 1H, HC=N) ppm. 13C
NMR (75 MHz, CDCl3): δ = 166.4, 153.7, 141.5, 134.3,
130.9, 129.1, 128.6, 124.8, 120.9, 120.7, 117.4,
62.1 ppm. HRMS: m/z Calcd for C18H14N2O3 (M + H)+
307.1083; Found 307.1080.
(E)-1-(4-((4-Trifluorobenzylidene)amino)phenyl)-1H-
pyrrole-2,5-dione (5i). Light yellow solid. mp 195–197°C.
Acknowledgments. A. R. is thankful to Sri Venkateswara
University for lab facilities, and G. M. R is grateful to Brazilian
Higher Education Personnel Training Coordination (CAPES:
Coordenação de Aperfeiçoamento de Pessoal de Nível Superior)
under PNPD program and Ural Federal University, Russia.
1H NMR (300 MHz, CDCl3): δ = 7.30–8.38 (m, 10H, Ar-
H), 9.36 (s, 1H, HC=N) ppm. 13C NMR (75 MHz, CDCl3):
δ = 164.7, 162.2, 141.2, 140.0, 137.3, 135.2, 132.7, 132.0,
129.6, 123.5, 123.3, 120.1 ppm. HRMS: m/z Calcd for
C18H11F3N2O2 (M + H)+ 345.0851; Found 345.0847.
REFERENCES AND NOTES
[1] Rocchi, D.; Gonza´ lez, J. F.; Mene´ ndez, J. C. Green Chem
2013, 15, 511.
Journal of Heterocyclic Chemistry
DOI 10.1002/jhet