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Volumn , Issue 11, 2007, Pages 1691-1694

One-pot synthesis of spiro pyrroloimidazoles and 2-arylimidazoles from 1,2-diaza-1,3-butadienes and arylamidines

Author keywords

1,2 diaza 1,3 butadienes; Arylamidines; Cyclizations; Nucleophilic additions; Spiro compounds

Indexed keywords

1,2 DIAZA 1,3 BUTADIENE DERIVATIVE; 2 ARYLIMIDAZOLE DERIVATIVE; AMIDINE; ARYLAMIDINE DERIVATIVE; IMIDAZOLE DERIVATIVE; PYRROLE DERIVATIVE; PYRROLOIMIDAZOLE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 34447558576     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-984508     Document Type: Article
Times cited : (11)

References (35)
  • 5
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    • Palacios, F.; Aparicio, D.; de los Santos, J. M. Tetrahedron 1999, 55, 13767.
    • (e) Palacios, F.; Aparicio, D.; de los Santos, J. M. Tetrahedron 1999, 55, 13767.
  • 13
    • 34447519240 scopus 로고    scopus 로고
    • Grimmet, M. R. Imidazoles In Comprehensive Heterocyclic Chemistry II, 3; Katritzky, A. R.; Rees, C. W.; Scriven, E. F. V., Eds.; Pergamon: London, 1996.
    • Grimmet, M. R. Imidazoles In Comprehensive Heterocyclic Chemistry II, Vol. 3; Katritzky, A. R.; Rees, C. W.; Scriven, E. F. V., Eds.; Pergamon: London, 1996.
  • 22
    • 34447543059 scopus 로고    scopus 로고
    • 2-EtOAc mixtures).
    • 2-EtOAc mixtures).
  • 23
    • 34447540267 scopus 로고    scopus 로고
    • Data for Methyl 7, Methoxycarbonyl)amino]-6-[2-(methoxycarbonyl) hydrazino]-6,8-dimethyl-4-oxo-2-phenyl-1,3,7-triazaspiro[4.4]nona-1, 8-diene-9-carboxylate (3b) 5R/S,6R/S-Isomer White powder from EtOAc-n-pentane, mp 161-163°C (dec, IR (Nujol, 3465, 3303, 3244, 3192, 1735, 1721, 1707, 1673, 1648, 1608, 1543, 1515 cm-1. 1H NMR (400 MHz, DMSO-d6, δ, 1.06 (s, 3 H, CH3, 2.10 (s, 3 H, CH3, 3.46 (s, 3 H, OCH3, 3.60 (s, 3 H, OCH3, 3.69 (s, 3 H, OCH3, 6.13 (s, 1 H, NH, 7.53 (t, J, 7.6 Hz, 2 H, Ar, 7.60 (t, J, 7.6 Hz, 1 H, Ar, 7.98 (d, J, 7.6 Hz, 2 H, Ar, 8.27 (s, 1 H, NH, 8.81 (s, 1 H, NH, 11.88 (s, 1 H, NH, 13C NMR 100 MHz DMSO-d6, δ, 11.58, 16.47, 50.31, 52.34, 81.45, 88.87, 96.90, 126.86, 128.37, 128.78, 131.82, 156.29, 156.95, 158.41, 163.86, 184.58. MS: m/z, 460 [M
    • 7: C, 52.17; H, 5.25; N, 18.25. Found: C, 52.16; H, 5.23; N, 18.26.
  • 26
    • 34447560093 scopus 로고    scopus 로고
    • + + 1] (0.5), 260 (3), 216 (12), 202 (57), 104 (100).
    • + + 1] (0.5), 260 (3), 216 (12), 202 (57), 104 (100).
  • 27
    • 34447508366 scopus 로고    scopus 로고
    • Crystallographic data (excluding structure factors) for compound 3b and 4c have been deposited at the Cambridge Crystallographic Data Centre as supplementary publication number CCDC 637246 and 637245. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: +44 (1223)336033 or e-mail: deposit@ccdc.cam.ac.uk].
    • Crystallographic data (excluding structure factors) for compound 3b and 4c have been deposited at the Cambridge Crystallographic Data Centre as supplementary publication number CCDC 637246 and 637245. Copies of the data can be obtained, free of charge, on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK [fax: +44 (1223)336033 or e-mail: deposit@ccdc.cam.ac.uk].
  • 28
    • 34447502456 scopus 로고    scopus 로고
    • 2-EtOAc mixtures).
    • 2-EtOAc mixtures).
  • 29
    • 34447506606 scopus 로고    scopus 로고
    • Data for N,N-Diethyl-5-methyl-2-phenyl-1H-imidazole-4-carboxamide (4c) Colorless crystals from Et 2O, mp 187-190°C. IR (Nujol, 3114, 1595, 1566, 1538, 1494 cm-1. 1H NMR (400 MHz, DMSO-d6, δ, 1.14 (br s, 3 H, CH3, 1.23 (br s, 3 H, CH3, 2.40 (s, 3 H, CH3, 3.37 (br s, 2 H, NCH2, 3.77 (br s, 2 H, NCH2, 7.34 (t, J, 7.6 Hz, 1 H, Ar, 7.45 (t, J, 7.6 Hz, 2 H, Ar, 7.90 (d, J, 7.6 Hz, 2 H, Ar, 12.59 (s, 1 H, NH, 13C NMR (100 MHz DMSO-d6, δ, 10.84, 12.97, 14.68, 39.66, 42.45, 124.59, 128.01, 128.70, 130.33, 132.54, 132.76, 142.21, 164.12. MS: m/z, 257 [M, 27, 185 (100, 158 99, Anal. Calcd for C15H19N3O: C, 70.01; H, 7.44; N, 16.33. Found: C, 69.99; H, 7.47; N, 16.35
    • 3O: C, 70.01; H, 7.44; N, 16.33. Found: C, 69.99; H, 7.47; N, 16.35.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.