메뉴 건너뛰기
Synlett
Volumn , Issue 8, 2007, Pages 1231-1234
A versatile synthetic approach to isoguanine derivatives
Author keywords

Heterocycles; Imidazole; Isoguanine; Rearrangements; Ring closure
Indexed keywords

5 AMINO 4 (N ETHOXYCARBONYL)CYANOFORMIDOYL IMIDAZOLE; 5 AMINO 4 (N ETHOXYCARBONYL)FORMAMIDINO IMIDAZOLE; ACETONITRILE; ALCOHOL; AMINE; GUANINE DERIVATIVE; IMIDAZOLE DERIVATIVE; ISOGUANINE DERIVATIVE; SULFURIC ACID; UNCLASSIFIED DRUG;
EID: 34249783461     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-977419     Document Type: Article
Times cited : (11)
References (39)
  • 37
    • 34249816582 scopus 로고    scopus 로고
    • Compounds 3 Aqueous methylamine (for 3a and 3b, 14 equiv, or benzylamine (for 3c and 3d, 2-3 equiv) was added to a suspension of imidazole 2 in CH2Cl2 (for 3a and 3b, EtOH (for 3c, or MeCN (for 3d, 2-12 mL, The mixture was stirred at r.t. for 10 min to 18 h. The product precipitated from the reaction mixture (3c and 3d) or the solvent was removed in the rotary evaporator (3a and 3b) and EtOH was added to the residue. The white solid was filtered and washed with EtOH (3a-c, or MeCN(3d, and Et2O. The structure of the products obtained was confirmed by elemental analysis, 1H NMR and 13C NMR spectroscopy. Characterization of 3a 1H NMR (300 MHz, DMSO-d6, 20 °C, δ (mixture of conformers A and B, ratio A/B, 3:2, 9.90 (br s, 1 H, A, 8.00 (br s, 1 H, B, 7.40 d, J
    • 3: C, 56.77; H, 6.04; N, 22.07. Found: C, 56.97; H, 6.06; N, 21.57. IR (mull): 3251 (m), 3116 (m), 1640 (s), 1598 (s).
  • 38
    • 34249774668 scopus 로고    scopus 로고
    • Compounds 5 A suspension of 3a-d in EtOH (20-60 mL) was refluxed for 5 h to 4 d. The resulting suspension was filtered and washed with MeCN (4 and 5a, EtOH (4 and 5b and d) or Et2O (4 and 5c) to give a mixture of compounds 4 and 5 in a ratio of 4.5:5.5 (4a:5a, 3:7 (4b:5b, 2.5:7.5 (4c:5c) and 2:8 (4d:5d, The mixture 4a:5a (4.5:5.5) was suspended in H2O and combined with KOH (1 N, The suspension was stirred at r.t. for 45 min to give a 2:8 mixture of 4a:5a. A suspension of these solid mixtures in EtOH (for a and c) or DMF (for b and d) was combined with DBU (1 equiv in relation to the amount of compound 4, The suspension was stirred at 40 °C for 6-18 h (a and b, or at r.t. for 30 min c and d, The white solid was filtered and washed with EtOH and Et2O to give compo
    • 7; C, 57.56; H, 4.83; N, 25.82. Found: C, 57.60; H, 5.06; N, 25.78. IR (mull): 3385 (m), 3208 (s), 3120 (s), 3052 (s), 1883 (w), 1698 (s), 1640 (s), 1601 (s), 1584 (s).
  • 39
    • 34249819756 scopus 로고    scopus 로고
    • Compounds 4 To a suspension of imidazole 3a-d in MeCN (8-10 mL) was added H2SO4 (1 equiv, and the mixture was refluxed for 18 h to 11 d. The resulting suspension was filtered and washed with MeCN (6a) or EtOH (6b) and Et2O. Then, DBU (1 equiv) was added to a suspension of compound 6a,b in MeCN (3-20 mL, The mixture was stirred at r.t. for 30 min to 3 h, when the white solid was filtered and washed with MeCN and Et2O, to give compounds 4a,b. The structure of the prdducts obtained was confirmed by elemental analysis, 1H NMR and 13C NMR spectroscopy. Characterization of 4a 1H NMR (300 MHz, DMSO-d6, δ, 10.70 (v br s, 1 H, 8.08 (s, 1 H, 8.00 (br s, 1 H, 7.64 (d, J, 9.0 Hz, 2 H, 7.08 (d. J, 9.0 Hz, 2 H, 3.80 (s, 3 H, 2.93 br s, 3 H, The compound 4a was not soluble in DMSO-d6 and the 13
    • 2O: C, 56.07; H, 4.99; N, 25.15. Found: C, 55.95; H, 4.92; N, 25.12. IR (mull): 3234 (s), 3126 (m), 3053 (m), 2733 (m), 1681 (s), 1626 (s), 1596 (s).

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.