Chemistry Of N-Heterocyclic Compounds : Part I: Regioselective Synthesis Of Macrocycles Containing 4-Amino-L,2,4-Triazoles

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• Data for compound 3 : MP (190°C) (DMF), Yield (65%), 1H−NMR (300 MHz, d6 − DMSO) : 8 2.135 (q, J = 6.4Hz, 2H, −C−CH2−C); 3.188 (t, J=6.4 Hz, 4H, 2x−SCH2); 5.668 (s, 4H, 2x−NH2); 13.7 (s, 2H, −NHC=S). 13C−NMR (300 MHz; d6− DMSO) : 28.446 (C−CH2−C−), 28.665 (−CH2−S), 149 979 (C=N), 167.337 (C=S) ppm. Elemental Analysis ‘(cal)/obs’: C (25.00%) /24.91%, H (35.7)/35.60, N (33.33%) / 33.28%, S (38.09%)/38.00%
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• Data for compound 4 : MP (195°C)(DMSO), Yield(35%), 1H−NMR (300 MHz, d6−DMSO). δ 2.139 (p, J = 6.4 Hz, 4H, 4x−C−CH2−C−), 3.211 (t, J = 6.4 Hz, 8H, 4x−S−CH2), 5.978 (s, 4H, 2x−NH2), 13C−NMR (300 MHz; d6−DMSO) : 29.560 (2x−C−CH2−C); 30.644 (4x−S−CH2) & 153.092 ppm (4 × C=N). M+, m/z 376 (6%). Elemental Analysis ‘(cal)/obs’ : C(31.91%)/31.87%, H (4.25%) / 4.21%, N (29.78%) / 29.69%, S (34.04%) / (34.00)
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• Data for compound 7 : MP (174°C)(DMF), Yield(70%), 1H−NMR (500 MHz, d6−DMSO) : δ 3.224 (t, J = 6.5 Hz, 4H, 2x−SCH2); 5.921 (s, 4H, 2x−NH2); 13.7888 (s, 2H, −NHC=S). 13C−NMR (500MHz, d6−DMSO); 34.864 (−CH2−S−), ?54.765(C=N), 172.750 (C=S) ppm. Elemental Analysis ‘(cal)/obs’ : C (22 36%) / 22.28%, H (3.10%) / 3.01%, N (34.78%) / 34.66%, S (39.75%)/39.71%
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• Data for compound 6 : MP (177°C) (DMSO) Yield (27%) : 1 H −NMR : (300 MHz; d6 − DMSO); δ 2.140 (q, J = 6.4 Hz, 2H −C−CH2−C), 3 205 (t, J = 6.4 Hz. 4H, 2x−CH2), 3.692 (s, 4H, 2x−C−CH2−S), 6.2 (s, 4H, 2x −NH2). 13C−NMR could not be scanned due to poor solubility Mf : m/z 362 (1%). Elemental Analysis ‘(cal)/obs’ : C (29.83%) / 29.72%, H (3.86%) / 3.81%, N (30.93%) / 30.80%, S (35.35%) / 35.21%
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• Data for compound 8. MP (220°C) (DMSO) Yield (20%) ‘H−NMR (300 MHz, d6 − DMSO) : δ 3.446 (s, 8H, 4x −CH2), 5.656 and 5.968 (s, 2H, −NH2). 13C−NMR could not be scanned due to poor solubility. M+ : m/z 348 (52%). Elemental Analysis ‘(cal)/obs’ : C (27.58%) / 27.51%, H (3.44%) / 3.39%, N (32.18%) / 32.11%, S (36.76%) / 36.67 %
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