메뉴 건너뛰기




Volumn 14, Issue 1, 2009, Pages 78-88

Synthesis of 5-substituted 3-amino-1H-pyrazole-4-carbonitriles as precursors for microwave assisted regiospecific syntheses of pyrazolo[1,5-a]pyrimidines

Author keywords

2 aroyl 3 dimethylamino 2 propenenitrile; 1H 15N HMBC; Oxoalkanonitriles; Pyrazolo 1,5 a pyrimidines; Solvent free reactions

Indexed keywords

ACETAMIDE DERIVATIVE; ALKANE; HYPNOTIC SEDATIVE AGENT; NITRILE; PYRAZOLE; PYRAZOLE DERIVATIVE; PYRIMIDINE DERIVATIVE; ZALEPLON;

EID: 58949103721     PISSN: None     EISSN: 14203049     Source Type: Journal    
DOI: 10.3390/molecules14010078     Document Type: Article
Times cited : (20)

References (19)
  • 1
    • 2942588972 scopus 로고    scopus 로고
    • Optimization of 3-phenylpyrazolo[1,5-a]pyrimidines as potent corticotrophin-releasing factor-1 antagonists with adequate lipophilicity and water solubility
    • Chen, C.; Wilcoxen, K. M.; Huang, C. Q.; McCarthy, J. R.; Chen, T.; Grigoriadis, D. E. Optimization of 3-phenylpyrazolo[1,5-a]pyrimidines as potent corticotrophin-releasing factor-1 antagonists with adequate lipophilicity and water solubility. Bioorg. Med. Chem. Lett. 2004, 14, 3669-3673.
    • (2004) Bioorg. Med. Chem. Lett , vol.14 , pp. 3669-3673
    • Chen, C.1    Wilcoxen, K.M.2    Huang, C.Q.3    McCarthy, J.R.4    Chen, T.5    Grigoriadis, D.E.6
  • 2
    • 4444342110 scopus 로고    scopus 로고
    • Design, synthesis, and hypnotic activity of pyrazolo[1,5-a]pyrimidine derivatives
    • Wang, S. Q.; Fang, L.; Liu, X. J.; Zhao, K. Design, synthesis, and hypnotic activity of pyrazolo[1,5-a]pyrimidine derivatives. Chin. Chem. Lett. 2004, 15, 885-888.
    • (2004) Chin. Chem. Lett , vol.15 , pp. 885-888
    • Wang, S.Q.1    Fang, L.2    Liu, X.J.3    Zhao, K.4
  • 3
    • 0035540383 scopus 로고    scopus 로고
    • Aminoazoles in heterocycles synthesis: II. Trifluoromethyl-containing diketones in the synthesis of pyrazolo[1,5-a]pyrimidines
    • Emelina, E. E.; Petrov, A. A.; Firsov, A. V. Aminoazoles in heterocycles synthesis: II. Trifluoromethyl-containing diketones in the synthesis of pyrazolo[1,5-a]pyrimidines. Russ. J. Org. Chem. 2001, 37, 852-858.
    • (2001) Russ. J. Org. Chem , vol.37 , pp. 852-858
    • Emelina, E.E.1    Petrov, A.A.2    Firsov, A.V.3
  • 4
    • 33745968178 scopus 로고    scopus 로고
    • Management of chronic insomnia in elderly persons
    • Bain, K. T. Management of chronic insomnia in elderly persons. Am. J. Geriatr. Pharmacother. 2006, 4, 168-192.
    • (2006) Am. J. Geriatr. Pharmacother , vol.4 , pp. 168-192
    • Bain, K.T.1
  • 5
    • 4243057381 scopus 로고    scopus 로고
    • Comparative efficacy of newer hypnotic drugs for the short-term management of insomnia: A systematic review and meta-analysis
    • Dundar,Y.; Dodd, S.; Strobl, J.; Boland, A.; Dickson, R.; Walley, T. Comparative efficacy of newer hypnotic drugs for the short-term management of insomnia: a systematic review and meta-analysis. Hum. Psychopharmacol. 2004, 19, 305-322.
    • (2004) Hum. Psychopharmacol , vol.19 , pp. 305-322
    • Dundar, Y.1    Dodd, S.2    Strobl, J.3    Boland, A.4    Dickson, R.5    Walley, T.6
  • 6
    • 1842783143 scopus 로고    scopus 로고
    • Electroencephalographic properties of zaleplon, a non-benzodiazepine sedative/hypnotic, in rats
    • Noguchi, H.; Kitazumi, K.; Mori, M.; Shiba, T. Electroencephalographic properties of zaleplon, a non-benzodiazepine sedative/hypnotic, in rats. J. Pharmacol. Sci. 2004, 94, 246-251.
    • (2004) J. Pharmacol. Sci , vol.94 , pp. 246-251
    • Noguchi, H.1    Kitazumi, K.2    Mori, M.3    Shiba, T.4
  • 7
    • 34248536361 scopus 로고
    • Nitriles in organic synthesis: The reaction of trichloroacetonitrile with active methylene reagents
    • Ibrahim, N. S.; Abdelrazek, F. M.; Aziz, S. I.; Elnagdi, M. H.; Nitriles in organic synthesis: the reaction of trichloroacetonitrile with active methylene reagents. Monatsh. Chem. 1985, 116, 551-556.
    • (1985) Monatsh. Chem , vol.116 , pp. 551-556
    • Ibrahim, N.S.1    Abdelrazek, F.M.2    Aziz, S.I.3    Elnagdi, M.H.4
  • 8
    • 37249075344 scopus 로고    scopus 로고
    • Pyrolytic methods in organic synthesis: Novel routes for the synthesis of 3-oxoalkanenitriles, 2-acyl anilines, and 2-aroyl anilines
    • Al-Awadi, N. A.; Abdelkhalik, M. M.; Abdelhamid, I. A.; Elnagdi, M. H. Pyrolytic methods in organic synthesis: novel routes for the synthesis of 3-oxoalkanenitriles, 2-acyl anilines, and 2-aroyl anilines. Synlett. 2007, 19, 2979-2982.
    • (2007) Synlett , vol.19 , pp. 2979-2982
    • Al-Awadi, N.A.1    Abdelkhalik, M.M.2    Abdelhamid, I.A.3    Elnagdi, M.H.4
  • 9
    • 34547661632 scopus 로고
    • A novel preparation of polarized ethylenes by the reaction of thioamides or dithiocarboxylates with tetracyanoethylene oxide. Synthesis of pyrazoles and pyrimidines
    • Tominaga, Y.; Matsuoka, Y.; Kohra, S.; Hosomi, A. A novel preparation of polarized ethylenes by the reaction of thioamides or dithiocarboxylates with tetracyanoethylene oxide. Synthesis of pyrazoles and pyrimidines. Heterocycles 1987, 26, 613-616.
    • (1987) Heterocycles , vol.26 , pp. 613-616
    • Tominaga, Y.1    Matsuoka, Y.2    Kohra, S.3    Hosomi, A.4
  • 10
    • 0016831269 scopus 로고
    • Preparation of 4,6-diaminopyrazolo[3,4- d]pyrimidines with variations in substitutions at the 1- and 3-positions
    • Southwick, P. L.; Dhawan, B. Preparation of 4,6-diaminopyrazolo[3,4- d]pyrimidines with variations in substitutions at the 1- and 3-positions. J. Heterocycl. Chem. 1975, 12, 1199-1205.
    • (1975) J. Heterocycl. Chem , vol.12 , pp. 1199-1205
    • Southwick, P.L.1    Dhawan, B.2
  • 11
    • 33748959384 scopus 로고    scopus 로고
    • New regiospecific isothiazole C-C coupling chemistry
    • Chritoforou, I. C.; Koutentis, P. A.; New regiospecific isothiazole C-C coupling chemistry Org. Biomol. Chem. 2006, 4, 3681-3693.
    • (2006) Org. Biomol. Chem , vol.4 , pp. 3681-3693
    • Chritoforou, I.C.1    Koutentis, P.A.2
  • 12
    • 43649101047 scopus 로고    scopus 로고
    • Studies with functionally substituted enamines: Synthesis of 2-aroyl-3-dimethylamino-2- propenenitrile and their reactivity toward nitrogen nucleophiles
    • Al-Qalaf, F.; Abdelkhalik, M. M.; Al-Enzy, A.; Al-Agamy, G. Studies with functionally substituted enamines: synthesis of 2-aroyl-3-dimethylamino-2- propenenitrile and their reactivity toward nitrogen nucleophiles. Heterocycles 2008, 75, 145-156.
    • (2008) Heterocycles , vol.75 , pp. 145-156
    • Al-Qalaf, F.1    Abdelkhalik, M.M.2    Al-Enzy, A.3    Al-Agamy, G.4
  • 13
    • 0001727959 scopus 로고
    • Chemistry of pyrazolopyrimidines
    • Katritzky, A. R, Ed, Academic Press Inc, New York, USA
    • Elnagdi, M. H.; Elmoghayar, M. R. H.; Elgemeie, G. E. H. Chemistry of pyrazolopyrimidines. In Advances in Heterocyclic Chemistry; Katritzky, A. R., Ed.; Academic Press Inc.: New York, USA, 1987; Vol. 41, pp. 319-376.
    • (1987) Advances in Heterocyclic Chemistry , vol.41 , pp. 319-376
    • Elnagdi, M.H.1    Elmoghayar, M.R.H.2    Elgemeie, G.E.H.3
  • 14
    • 84988115615 scopus 로고
    • Preparation and characterization of pyrazolo[1,5-a] pyrimidines
    • Maquestiau, A.; Target, H.; Van Den Eyden, J. J. Preparation and characterization of pyrazolo[1,5-a] pyrimidines. Bull. Soc. Chim. Belg. 1992, 101, 131-136.
    • (1992) Bull. Soc. Chim. Belg , vol.101 , pp. 131-136
    • Maquestiau, A.1    Target, H.2    Van Den Eyden, J.J.3
  • 16
    • 84882743371 scopus 로고    scopus 로고
    • 2H-Pyrazol-3-ylamines as precursors for the synthesis of polyfunctionally substituted pyrazolo[1,5-a]pyrimidines
    • Anwar, H. F.; Fleita, D. H.; Kolshorn, H.; Meier, H.; Elnagdi, M. H. 2H-Pyrazol-3-ylamines as precursors for the synthesis of polyfunctionally substituted pyrazolo[1,5-a]pyrimidines. Arkivoc 2006, (xv), 133-141.
    • (2006) Arkivoc , vol.15 , pp. 133-141
    • Anwar, H.F.1    Fleita, D.H.2    Kolshorn, H.3    Meier, H.4    Elnagdi, M.H.5
  • 17
    • 34247354886 scopus 로고    scopus 로고
    • α-Aminoazoles in syntheses of heterocycles: 3(5)-aminopyrazole-4-carbonitriles in the synthesis of pyrazolo[1,5-a]pyrimidines
    • Emelina, E. E.; Petrov, A. A.; Firsov, A.V. α-Aminoazoles in syntheses of heterocycles: 3(5)-aminopyrazole-4-carbonitriles in the synthesis of pyrazolo[1,5-a]pyrimidines. Russ. J. Org. Chem. 2007, 43, 471-473.
    • (2007) Russ. J. Org. Chem , vol.43 , pp. 471-473
    • Emelina, E.E.1    Petrov, A.A.2    Firsov, A.V.3
  • 18
    • 59349116911 scopus 로고    scopus 로고
    • Microwaves in chemical synthesis
    • 3rd Ed, Hall, N, Ed, Cambridge University Press: Cambridge, MA, USA, Chapter 4, pp
    • rd Ed.; Hall, N., Ed.; Cambridge University Press: Cambridge, MA, USA, 2000; Chapter 4, pp. 67-75.
    • (2000) The New Chemistry , pp. 67-75
    • Michael, D.1    Mingos, P.2    Baghurst, D.R.3
  • 19
    • 59349094279 scopus 로고    scopus 로고
    • Microwave activation of catalytic reactions
    • Loupy, A, Ed, WILEY-VCH Verlag GmbH & Co: Weinheim, Germany, Chapter 13, pp
    • Hájek, M.; Microwave activation of catalytic reactions. In Microwaves in Organic Synthesis; Loupy, A., Ed.; WILEY-VCH Verlag GmbH & Co: Weinheim, Germany, 2006; Vol. 2, Chapter 13, pp. 634-637.
    • (2006) Microwaves in Organic Synthesis , vol.2 , pp. 634-637
    • Hájek, M.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.