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Volumn 50, Issue 5, 2013, Pages 1187-1197

Efficient new synthesis of N-arylbenzo[b]furo[3,2-d]pyrimidin-4-amines and their benzo[b]thieno[3,2-d]pyrimidin-4-amine analogues via a microwave-assisted Dimroth rearrangement

Author keywords

[No Author keywords available]

Indexed keywords

2 MORPHOLINO 8 PHENYLCHROMONE; 3 (4 NITROPHENYL)BENZO[B]FURO[3,2 D]PYRIMIDIN 4(3H) IMINE; 3 AMINO 2 CYANOBENZO[B]FURANE; 3 AMINO 2 CYANOBENZO[B]THIOPHENE; 4 (BENZO[4,5]THIENO[3,2 D]PYRIMIDIN 4 YLAMINO) 2 NITROPHENOL; 4 (BENZOFURO[3,2 D]PYRIMIDIN 4 YLAMINO) 2 NITROPHENOL; BENZO[B]FURO[3,2 D]PYRIMIDIN 4 AMINE; BENZO[B]THIENO [3,2 D]PYRIMIDIN 4 AMINE; N (2,3 DIHYDROBENZO[B][1,4]DIOXIN 6 YL)BENZO[4,5]THIENO[3,2 D]PYRIMIDIN 4 AMINE; N (2,3 DIHYDROBENZO[B][1,4]DIOXIN 6 YL)BENZOFURO[3,2 D]PYRIMIDIN 4 AMINE; N (3 CHLORO 4 FLUOROPHENYL)BENZO[B]FURO[3,2 D]PYRIMIDIN 4 AMINE; N (3 CHLORO 4 FLUOROPHENYL)BENZO[B]THIENO[3,2 D]PYRIMIDIN 4 AMINE; N (3,4 DIMETHOXYPHENYL)BENZO[B]FURO[3,2 D]PYRIMIDIN 4 AMINE; N (3,4 DIMETHOXYPHENYL)BENZO[B]THIENO[3,2 D]PYRIMIDIN 4 AMINE; N (3,4,5 TRIMETHOXYPHENYL)BENZO[B]FURO[3,2 D]PYRIMIDIN 4 AMINE; N (3,4,5 TRIMETHOXYPHENYL)BENZO[B]THIENO[3,2 D]PYRIMIDIN 4 AMINE; N (3,5 DIMETHOXYPHENYL)BENZO[B]FURO[3,2 D]PYRIMIDIN 4 AMINE; N (3,5 DIMETHOXYPHENYL)BENZO[B]THIENO[3,2 D]PYRIMIDIN 4 AMINE; N (4 BROMO 2 FLUOROPHENYL)BENZO[B]FURO[3,2 D]PYRIMIDIN 4 AMINE; N (4 BROMO 2 FLUOROPHENYL)BENZO[B]THIENO[3,2 D]PYRIMIDIN 4 AMINE; N (4 METHOXYPHENYL)BENZO[B]FURO[3,2 D]PYRIMIDIN 4 AMINE; N (4 METHOXYPHENYL)BENZO[B]THIENO[3,2 D]PYRIMIDIN 4 AMINE; N (BENZO[D][1,3]DIOXOL 5 YL)BENZO[4,5]THIENO[3,2 D]PYRIMIDIN 4 AMINE; N (BENZO[D][1,3]DIOXOL 5 YL)BENZOFURO[3,2 D]PYRIMIDIN 4 AMINE; N ARYLBENZO[B]FURO[3,2 D]PYRIMIDIN 4 AMINE; N PHENYLBENZO[B]FURO[3,2 D]PYRIMIDIN 4 AMINE; N PHENYLBENZO[B]THIENO[3,2 D]PYRIMIDIN 4 AMINE; N' (2 CYANOBENZO[B]FURAN 3 YL) N,N DIMETHYLFORMIMIDAMIDE; N' (2 CYANOBENZO[B]THIOPHEN 3 YL) N,N DIMETHYLFORMIMIDAMIDE; PYRIMIDINE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 84884902800     PISSN: 0022152X     EISSN: 19435193     Source Type: Journal    
DOI: 10.1002/jhet.1716     Document Type: Article
Times cited : (9)

References (32)
  • 8
    • 84884904796 scopus 로고    scopus 로고
    • (b) US Patent 0 143 399 A1, 2009
    • (b) US Patent 0 143 399 A1, 2009; Chem Abstr 2009, 151, 8539.
    • (2009) Chem Abstr , vol.151 , pp. 8539
  • 10
    • 84944488817 scopus 로고
    • (a), This paper is considered as the first paper of Otto Dimroth reporting the translocation of endocyclic and exocyclic nitrogen atoms with certain 1,2,3-triazoles. Since the work of Tsou and his co-workers [5b] in 2001, this reaction becomes very popular in medicinal chemistry[5c-h], e.g. for the synthesis of 4-substituted bioactive quinazolines (References [5c,g,h] are also focused on microwave-assisted methods)
    • (a), Dimroth, O., Liebigs Ann Chem 1909, 364, 183. This paper is considered as the first paper of Otto Dimroth reporting the translocation of endocyclic and exocyclic nitrogen atoms with certain 1,2,3-triazoles. Since the work of Tsou and his co-workers [5b] in 2001, this reaction becomes very popular in medicinal chemistry[5c-h], e.g. for the synthesis of 4-substituted bioactive quinazolines (References [5c,g,h] are also focused on microwave-assisted methods)
    • (1909) Liebigs Ann Chem , vol.364 , pp. 183
    • Dimroth, O.1
  • 20
    • 0345613203 scopus 로고
    • This paper described the synthesis of 1a and 8 using a Dimroth rearrangement form 3-(ethoxymethylene)amino-2-benzo[b]furocarbonitrile. Only one other aromatic aniline (p-chloro) derivative was also described
    • Sangapure, S. S.; Agasimundin, Y. S,. Indian J Chem B 1980, 19B, 115. This paper described the synthesis of 1a and 8 using a Dimroth rearrangement form 3-(ethoxymethylene)amino-2-benzo[b]furocarbonitrile. Only one other aromatic aniline (p-chloro) derivative was also described.
    • (1980) Indian J Chem B , vol.19 B , pp. 115
    • Sangapure, S.S.1    Agasimundin, Y.S.2
  • 22
    • 0030828376 scopus 로고    scopus 로고
    • For a synthesis of this reactant, see
    • For a synthesis of this reactant, see, Klose, J.; Reese, C. B.; Song, Q., Tetrahedron 1997, 53, 14411.
    • (1997) Tetrahedron , vol.53 , pp. 14411
    • Klose, J.1    Reese, C.B.2    Song, Q.3
  • 24
    • 0032330265 scopus 로고    scopus 로고
    • Lost dissipation factor (tan δ) expresses the capacity of a molecule or a material to transform electromagnetic energy into thermal energy. A high susceptibility to microwaves is characterized by a high value of tan δ. In the case of acetic acid, it is similar to the value of water (0.123 at 2.45 GHz), allowing convenient heating. For more details, see
    • Lost dissipation factor (tan δ) expresses the capacity of a molecule or a material to transform electromagnetic energy into thermal energy. A high susceptibility to microwaves is characterized by a high value of tan δ. In the case of acetic acid, it is similar to the value of water (0.123 at 2.45 GHz), allowing convenient heating. For more details, see, Gabriel, C., Gabriel, S., Grant, E. J., Halstead, B. S., Mingos, D. M. P., Chem Soc Rev 1998, 27, 213.
    • (1998) Chem Soc Rev , vol.27 , pp. 213
    • Gabriel, C.1    Gabriel, S.2    Grant, E.J.3    Halstead, B.S.4    Mingos, D.M.P.5
  • 25
    • 0019127671 scopus 로고
    • The synthesis of this product was described via another route in
    • The synthesis of this product was described via another route in, Robba, M.; Touzot, P.; El-Kashef, H., J Heterocyclic Chem 1980, 17, 923.
    • (1980) J Heterocyclic Chem , vol.17 , pp. 923
    • Robba, M.1    Touzot, P.2    El-Kashef, H.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.