An efficient three-component synthesis of 3-(1-Hydroxyalkyl)[1,2,4]- triazolo[4,3- c ]quinazolines

Synlett

Volumn , Issue 6, 2010, Pages 921-923

  Adib, Mehdi ^a   Ansari, Samira ^a   Feizi, Shahzad ^a   Bijanzadeh, Hamid Reza ^b  

^a UNIVERSITY OF TEHRAN   (Iran)

^b TARBIAT MODARES UNIVERSITY   (Iran)

Author keywords

3 (1 hydroxyalkyl) 1,2,4 triazolo 4,3 c quinazolines; 4(3 H) quinazolinones; Aldehydes; Cyclizations; Heterocycles; Multicomponent reactions; N isocyaniminotriphenylphosphorane

Indexed keywords

4 (3H)QUINAZOLINONE; N ISOCYANIMINOTRIPHENYLPHOSPHORANE; PHOSPHORANE DERIVATIVE; QUINAZOLINE DERIVATIVE; QUINAZOLINONE DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; CHEMICAL STRUCTURE; COMPLEX FORMATION; CYCLIZATION; CYCLOADDITION; DRUG SYNTHESIS; ONE POT SYNTHESIS; SYNTHESIS; THREE COMPONENT SYNTHESIS;

EID: 77949897780     PISSN: 09365214     EISSN: 14372096     Source Type: Journal    
DOI: 10.1055/s-0029-1219562     Document Type: Article

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41. General Procedure for the Preparation of Compounds 4al A mixture of N-isocyaniminotriphenylphosphorane (1 mmol) and the appropriate aldehyde (1 mmol) was dissolved in hot THF (5 mL). Then the appropriate 4 (3H)-quinazolinone (1 mmol) was added to the reaction mixture which was refluxed for 3 h. Then, the solvent was removed under the reduced pressure, and the residue was purified by TLC using CHCl3EtOAc (3:1) as eluent. The solvent was removed, and the product was obtained as colorless crystals. 3-[1-Hydroxy-1-(4-fluorophenyl) methyl]-5-phenyl-[1,2,4]triazolo[4,3-c]quinazoline (4c) Yield 0.34 g (93%); colorless crystals; mp 192193 C. IR (KBr): 3266 (OH), 1609, 1515, 1374, 1332, 1264, 1211, 1187, 1156, 1106, 1056, 1019, 947, 863, 794, 769, 680 cm1. 1H NMR (500.1 MHz, DMSO-d6): d = 5.35 (br s, 1 H, CH), 6.02 (d, J = 4.6 Hz, 1 H, OH), 7.08 (dd, J = 8.8, 8.9 Hz, 2 H, 2× CH), 7.117.19 (m, 2 H, 2 ×CH), 7.567.66 (m, 4 H, 4×CH), 7.78 (dd, J = 6.8, 7.4 Hz, 2 H, 2 ×CH), 7.86 (dd, J = 7.3, 8.1 Hz, 1 H, CH), 7.96 (d, J = 8.1 Hz, 1 H, CH), 8.54 (d, J = 7.9 Hz, 1 H, CH). 13C NMR (125.8 MHz, DMSO-d6): d = 65.94 (CH), 114.46 (d, 2JFC = 21.4 Hz, CH), 115.94 (C), 122.56, 127.89, 128.28 and 128.73 (4 ×CH), 128.87 (d, 3JFC = 8.1 Hz, CH), 129.25, 130.63 and 131.83 (3 ×CH), 133.48 (C), 137.16 (d, 4JFC = 2.7 Hz, C), 140.33, 145.65, 148.88 and 150.75 (4 C), 161.45 (d, 1JCF = 243.2 Hz, CF). MS (EI): m/z (%) = 370 (6) [M+], 279 (20), 247 (12), 205 (9), 167 (23), 149 (100), 113 (10), 104 (9), 83 (9), 71 (18), 57 (29). Anal. Calcd for C22H15FN4O (370.38): C, 71.34; H, 4.08; N, 15.13. Found: C, 71.3; H, 4.2; N, 15.1. 3-[1-Hydroxy-1-(4-nitrophenyl)methyl]-5-(4-methylphenyl) [1,2,4]triazolo[4,3-c]quinazoline (4f) Yield 0.40 g (97%); colorless crystals; mp 228 C. IR (KBr): 3344 (OH), 1614, 1511, 1466, 1335, 1181, 1105, 1069, 1039, 986, 948, 818, 769, 696 cm1. 1H NMR (500.1 MHz, DMSO-d6): d = 2.42 (s, 3 H, CH3), 5.52 (d, J = 5.8 Hz, 1 H, CH), 6.25 (d, J = 5.8 Hz, 1 H, OH), 7.37 (d, J = 7.2 Hz, 2 H, 2 ×CH), 7.49 (d, J = 8.7 Hz, 2 H, 2 ×CH), 7.73 (d, J = 7.8 Hz, 2 H, 2 ×CH), 7.79 (dd, J = 7.4, 7.7 Hz, 1 H, CH), 7.88 (t, J = 7.1, 7.2 Hz, 1 H, CH), 7.98 (d, J = 8.1 Hz, 1 H, CH), 8.16 (d, J = 8.7 Hz, 2 H, 2 CH), 8.53 (d, J = 7.4 Hz, 1 H, CH). 13C NMR (125.8 MHz, DMSO-d6): d = 21.12 (CH3), 65.77 (CH), 115.83 (C), 122.61, 122.92, 127.93, 127.96, 128.75, 128.85, 129.26 (7 ×CH), 130.59 (C), 131.98 (CH), 140.48, 140.52, 145.81, 146.79, 148.70, 149.08 and 150.11 (7 ×C). MS (EI): m/z (%) = 411 (2) [M+], 386 (5), 370 (14), 277 (100), 247 (31), 205 (24), 183 (19), 152 (16), 123 (12), 97 (18), 77 (28). Anal. Calcd for C23H17N5O3 (411.41): C, 67.15; H, 4.16; N, 17.02. Found: C, 67.2; H, 4.2; N, 16.9.
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