Reaction between N-Isocyaniminotriphenylphosphorane, Aldimines, Meldrum’s
Acid and Water: Diastereoselective Synthesis of 3,4-Disubstituted N-Aminopyrrolidine-2,5-diones

Mehdi Adib; Samira Ansari; Hamid Reza Bijanzadeh

doi:10.1055/s-0030-1259696

LETTER

Reaction between N-Isocyaniminotriphenylphosphorane, Aldimines, Meldrum’s Acid and Water: Diastereoselective Synthesis of 3,4-Disubstituted N-Aminopyrrolidine-2,5-diones

Mehdi Adib*^a, Samira Ansari^a, Hamid Reza Bijanzadeh^b
^a School of Chemistry, University College of Science, University of Tehran, PO Box 14155-6455, Tehran, Iran
Fax: +98(21)66495291; e-Mail: madib@khayam.ut.ac.ir;
^b Department of Chemistry, Tarbiat Modarres University, PO Box 14115-175, Tehran, Iran

Abstract

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Abstract

A multicomponent synthesis of 3,4-disubstituted N-aminopyrrolidine-2,5-diones is described. A mixture of N-isocyaniminotriphenylphosphorane, an aldimine and Meldrum’s acid undergoes an addition reaction under mild conditions in aqueous THF to produce 1-amino-4-aryl-2,5-dioxo-N ^³-aryl-3-pyrrolidinecarboxamides diastereoselectively in good to excellent yields. ^¹H NMR analysis showed that the two substituents on C-3 and C-4 positions of the obtained pyrrolidine-2,5-diones are trans.

Key words

N-isocyaniminotriphenylphosphorane - aldimines - Meldrum’s acid - 3,4-disubstituted N-aminopyrrolidine-2,5-diones - diastereoselective synthesis - multicomponent reactions

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References and Notes

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General Procedure for the Preparation of Compounds 4a-i: A mixture of N-isocyaniminotriphenylphosphorane (1 mmol), the appropriate imine (1 mmol) and Meldrum’s acid (1 mmol) in THF (5 mL) was stirred at ambient temperature for 48 h. The progress of the reaction was monitored by TLC. Then, the solvent was removed under the reduced pressure and the residue was purified by column chromatography using n-hexane-EtOAc (3:1) as eluent. The solvent was removed and the product was recrystallized from n-hexane-EtOAc (1:1).
1-Amino-4-(4-methylphenyl)-2,5-dioxo- N ^³ -phenyl-3-pyrrolidinecarboxamide (4c):
yield: 0.28 g (86%); colorless crystal; mp 152-154 ˚C. IR (KBr): 3340, 3275, 3192 (NH), 1772, 1693 (C=O), 1600, 1534, 1438, 1312, 1191, 1106, 903, 815, 748, 691 cm^-¹. ^¹H NMR (500.1 MHz, DMSO-d ₆): δ = 2.28 (s, 3 H, Me), 4.01 (d, J = 5.0 Hz, 1 H, CH), 4.34 (d, J = 5.0 Hz, 1 H, CH), 5.16 (br s, 2 H, NH₂), 7.09 (t, J = 7.4 Hz, 1 H, CH), 7.17-7.21 (m, 4 H, 4 × CH), 7.33 (dd, J = 8.1, 7.7 Hz, 2 H, 2 × CH), 7.59 (d, J = 7.7 Hz, 2 H, 2 × CH), 10.49 (s, 1 H, NHCO). ^¹³C NMR (125.8 MHz, DMSO-d ₆): δ = 20.53 (Me), 47.26, 54.72 (2 × CH), 119.19, 123.97, 127.95, 128.79, 129.30 (5 × CH), 133.41, 137.02, 138.21 (3 × C), 164.82, 171.06, 174.59 (3 × C=O). EI-MS: m/z (%) = 323 (10) [M⁺], 279 (13), 236 (9), 203 (21), 167 (31), 149 (86), 115 (17), 97 (23), 83 (37), 71 (42), 69 (78), 57 (89), 55 (65), 43 (100), 41 (72). Anal. Calcd for C₁₈H₁₇N₃O₃ (323.35): C, 66.86; H, 5.30; N, 13.00. Found: C, 67.0; H, 5.4; N, 12.8.
1-Amino-4-(4-chlorophenyl)-2,5-dioxo- N ^³ -phenyl-3-pyrrolidinecarboxamide (4e): yield: 0.33 g (96%); colorless crystal; mp 172-174 ˚C. IR (KBr): 3321, 3234, 3172 (NH), 1787, 1704, 1667 (C=O), 1603, 1537, 1493, 1440, 1414, 1321, 1257, 1215, 1094, 1051, 1007, 965, 830, 790, 743, 693, 658 cm^-¹. ^¹H NMR (500.1 MHz, DMSO-d ₆): δ = 4.04 (d, J = 5.3 Hz, 1 H, CH), 4.45 (d, J = 5.3 Hz, 1 H, CH), 5.15 (s, 2 H, NH₂), 7.09 (t, J = 7.4 Hz, 1 H, CH), 7.33 (dd, J = 8.1, 7.7 Hz, 2 H, 2 × CH), 7.38 (d, J = 8.5 Hz, 2 H, 2 × CH), 7.45 (d, J = 8.5 Hz, 2 H, 2 × CH), 7.59 (d, J = 7.7 Hz, 2 H, 2 × CH), 10.50 (s, 1 H, NHCO). ^¹³C NMR (125.8 MHz, DMSO-d ₆): δ = 46.93, 54.39 (2 × CH), 119.30, 124.09, 128.76, 128.89, 130.25 (5 × CH), 132.56, 135.34, 138.27 (3 × C), 164.75, 171.00, 174.27 (3 × C=O). EI-MS: m/z (%) = 345 (13) [M⁺ + ^³7Cl], 343 (35) [M⁺ + ^³5Cl], 315 (31), 295 (11), 284 (7), 273 (17), 236 (15), 223 (53), 207 (32), 196 (29), 179 (24), 165 (48), 152 (17), 137 (33), 111 (22), 102 (33), 93 (47), 83 (43), 77 (45), 69 (80), 57 (100), 43 (98), 41 (84). Anal. Calcd for C₁₇H₁₄ClN₃O₃ (343.77): C, 59.40; H, 4.10; N, 12.22. Found: C, 59.4; H, 4.0; N, 12.1.

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