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Volumn , Issue 9, 2007, Pages 1431-1435

Novel solid-phase synthetic method for combinatorial generation of a 4-hydroxyquinolin-2(1H)-one-based library

Author keywords

Combinatorial chemistry; Cyclative cleavage; Dieckmann condensation; Quinolinone; Solid phase synthesis

Indexed keywords

4 HYDROXYQUINOLIN 2(1H) ONE DERIVATIVE; ANTHRANILIC ACID DERIVATIVE; POLYMER; QUINOLINOL DERIVATIVE; UNCLASSIFIED DRUG;

EID: 34250765381     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2007-980368     Document Type: Article
Times cited : (8)

References (64)
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    • Xu, C.; Yang, L.; Bhandari, A.; Holmes, C. P. Tetrahedron Lett. 2006, 47, 4885: The recent report described the solid-phase synthesis of 3-carbomethoxy-4-hydoxyquinolin-2(1H)-one bound to a resin through the bonding to nitrogen at 1-position as an intermediate resin for introduction of carbon-based substituents at 4-position of quinolin-2(1H)-one skeleton.
    • (b) Xu, C.; Yang, L.; Bhandari, A.; Holmes, C. P. Tetrahedron Lett. 2006, 47, 4885: The recent report described the solid-phase synthesis of 3-carbomethoxy-4-hydoxyquinolin-2(1H)-one bound to a resin through the bonding to nitrogen at 1-position as an intermediate resin for introduction of carbon-based substituents at 4-position of quinolin-2(1H)-one skeleton.
  • 31
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    • In addition to commercially available 2-nitrobenzoic acids, they can be prepared from the regioselective nitration of benzoic acids, the oxidation of o-nitrotoluenes, 2-nitrobenzyl alcohols, 2-nitrobenzaldehydes, and 2′-nitroacetophenones, and the substitutions of halogenated 2-nitrobenzoic acids. On the other hand, variation of the X group would be possible for the resin-bound 2-nitrobenzoic acid derivatives 6 and will be reported elsewhere. For examples of the nitration, see ref. 8d and: (a) Coppola, G. M, Schuster, H. F. J. Heterocycl. Chem. 1989, 26, 957
    • In addition to commercially available 2-nitrobenzoic acids, they can be prepared from the regioselective nitration of benzoic acids, the oxidation of o-nitrotoluenes, 2-nitrobenzyl alcohols, 2-nitrobenzaldehydes, and 2′-nitroacetophenones, and the substitutions of halogenated 2-nitrobenzoic acids. On the other hand, variation of the X group would be possible for the resin-bound 2-nitrobenzoic acid derivatives 6 and will be reported elsewhere. For examples of the nitration, see ref. 8d and: (a) Coppola, G. M.; Schuster, H. F. J. Heterocycl. Chem. 1989, 26, 957.
  • 35
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    • For examples of the oxidation, see: (e) Yamazaki, S. Synth. Commun. 1999, 29, 2211
    • For examples of the oxidation, see: (e) Yamazaki, S. Synth. Commun. 1999, 29, 2211.
  • 45
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    • For an example of the substitution, see ref. 4e
    • (o) For an example of the substitution, see ref. 4e.
  • 47
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    • With respect to acylation of N-alkylanthranilates with acetic acids, the conditions used in solution phase were pivaloyl chloride, pyridine, and MS in CH2Cl2 at r.t. for coupling of 2-methylaminobenzoates with thiocarbamoylacetic acids,6e EDC in THF at r.t. for reaction of 2-methylaminobenzoates with mono-tert-butyl malonate and cyanoacetic acid, and in POCl3 at 80°C for the reaction of benzyl 2-benzylaminobenzoate and (3-methylisoxazol-5-yl)acetic acid. See: (a) Blackburn, C, LaMarche, M. J, Brown, J, Che, J. L, Cullis, C. A, Lai, S, Maguire, M, Marsilje, T, Geddes, B, Govek, E, Kadambi, V, Doherty, C, Brian, D, Brodjian, S, Marsh, K. C, Collins, C. A, Kym, P. R. Bioorg. Med. Chem. Lett. 2006, 16, 2621
    • 3 at 80°C for the reaction of benzyl 2-benzylaminobenzoate and (3-methylisoxazol-5-yl)acetic acid. See: (a) Blackburn, C.; LaMarche, M. J.; Brown, J.; Che, J. L.; Cullis, C. A.; Lai, S.; Maguire, M.; Marsilje, T.; Geddes, B.; Govek, E.; Kadambi, V.; Doherty, C.; Brian, D.; Brodjian, S.; Marsh, K. C.; Collins, C. A.; Kym, P. R. Bioorg. Med. Chem. Lett. 2006, 16, 2621.
  • 50
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    • Since the seminal contributions of Rapoport to the solid-phase unidirectional Dieckmann reaction, Dieckmann-type condensation reaction has been utilized for the solid-phase synthesis of tetramic acid derivatives. See: a
    • Since the seminal contributions of Rapoport to the solid-phase unidirectional Dieckmann reaction, Dieckmann-type condensation reaction has been utilized for the solid-phase synthesis of tetramic acid derivatives. See: (a) Crowley, J. I.; Rapoport, H. J Am. Chem. Soc. 1970, 92, 6363.
    • (1970) J Am. Chem. Soc , vol.92 , pp. 6363
    • Crowley, J.I.1    Rapoport, H.2
  • 58
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    • For a recent review on cyclative cleavage strategy, see:, Bannwarth, W, Hinzen, B, Eds, Wiley-VCH: Weinheim
    • For a recent review on cyclative cleavage strategy, see: Pernerstorfer, J. In Combinatorial Chemistry; Bannwarth, W.; Hinzen, B., Eds.; Wiley-VCH: Weinheim, 2006, 111-142.
    • (2006) Combinatorial Chemistry , pp. 111-142
    • Pernerstorfer, J.1
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    • Another reason for selection of KHMDS as a standard base was the known favorable character of potassium enolates for O-alkylation, which is needed to obtain the 4-alkoxy derivatives in high purities through a subsequent in situ alkylation of the cleaved products. The study on the efficient alkylation is in progress using polymer-supported alkylating agents and will be reported elsewhere
    • Another reason for selection of KHMDS as a standard base was the known favorable character of potassium enolates for O-alkylation, which is needed to obtain the 4-alkoxy derivatives in high purities through a subsequent in situ alkylation of the cleaved products. The study on the efficient alkylation is in progress using polymer-supported alkylating agents and will be reported elsewhere.
  • 60
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    • Representative Procedure for Preparation of Compounds 9 Preparation of 2-Benzylaminobenzoate Resin (7a; X, H, R1, Ph) To a mixture of the resin 1a (X, H; 4.00 g, theoretically 3.59 mmol, prepared from Wang resin (1.00 mmol/g, and benzaldehyde (1.14 g, 10.8 mmol) in DCE (60 mL) at r.t. was added NaBH(OAc)3 (2.28 g, 10.8 mmol, The mixture was stirred at r.t. for 12 h and the resin was filtered, washed several times with CH2Cl2, DMF, MeOH, H2O, and MeOH, and dried in a vacuum oven to give 7a (4.30 g, 99, on-bead ATR-FTIR: 3365 (NH, 3025, 2922, 1680 (C=O, 1602, 1581, 1512, 1492, 1451, 1221, 1172, 1097, 822, 750, 697 cm-1. Preparation of 2-{Benzyl[3-(4-methoxyphenyl)acetyl] amino}benzoate Resin (8a; X, H, R1, Ph, R2, 4-MeOC 6H4) To a mixture of the resin 7a (X, H, R1, Ph; 1.00 g, theoretically 0.830 mmol) and 4-methoxyphen
    • +.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.