SCOPUS 정보 검색 플랫폼

Volumn , Issue 2, 2008, Pages 278-280

Synthesis of 1H-benzotriazoles via reductive amination on solid supports

Author keywords

Benzotriazoles; Imines; Nitrogen heterocycles; Reductive amination reaction; Solid phase synthesis

Indexed keywords

ANILINE DERIVATIVE; BENZOTRIAZOLE DERIVATIVE;

AMINATION; ARTICLE; CHEMICAL STRUCTURE; REDUCTION; SOLID PHASE SYNTHESIS; SUBSTITUTION REACTION;

EID: 38849165919 PISSN: 09365214 EISSN: None Source Type: Journal
DOI: 10.1055/s-2008-1032014 Document Type: Article

Times cited : (8)

References (14)

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2
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5
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- Avemaria, F.¹ Zimmermann, V.² Bräse, S.³

6
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- Merrifield resin (0.93 mmol/g) was obtained from Polymer Laboratories.
- Merrifield resin (0.93 mmol/g) was obtained from Polymer Laboratories.

7
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- Nicolaou, K. C, Hanko, R, Hartwig, W, Eds, Wiley-VCH: Weinheim, Chap. 4
- Dahmen, S.; Bräse, S. In Handbook of Combinatorial Chemistry; Nicolaou, K. C.; Hanko, R.; Hartwig, W., Eds.; Wiley-VCH: Weinheim, 2002, Chap. 4.
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8
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- Zimmermann, V.; Avemaria, F.; Bräse, S. J. Comb. Chem. 2007, 9, 200.
- (2007) J. Comb. Chem , vol.9 , pp. 200
- Zimmermann, V.¹ Avemaria, F.² Bräse, S.³

9
- 38849133053
- Representative Experimental Procedure:10 Resin: Resin 6 (0.600 g, 0.384 mmol, 1.0 equiv, 4-methoxybenzaldehyde (7i; 0.523 g, 3.84 mmol, 10 equiv) and molecular sieve (2 g) were suspended in anhyd toluene (15 mL) in a 20-mL glass vial and the vessel was sealed with a PTFE-coated cap. The mixture was heated at 80°C for 3 d and occasionally shaken through. After cooling, the resin was separated from the molecular sieve, filtered on a polypropylene plastic frit, subsequently roughly washed with anhyd acetone, CH2Cl2 and pentane and dried in air stream for 5 min. The molecular sieve was disposed and the glass vial was briefly rinsed with anhyd toluene. The resin was then immediately placed back into the glass vial, NaBH3CN (0.145 g, 3.84 mmol, 10 equiv) and anhyd toluene (15 mL) were added and the vessel was sealed. The mixture was heated at 80°C for another 3 d and occasionally shaken through. After cooling, t
- 1H NMR).

10
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- For leading references, see: (a) Review: Baxter, E. W.; Reitz, A. B. Org. React. (N. Y.) 2002, 59, 1.
- For leading references, see: (a) Review: Baxter, E. W.; Reitz, A. B. Org. React. (N. Y.) 2002, 59, 1.

11
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12
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- (c) DiCesare, J. C.; White, C. E.; Rasmussen, W. E.; White, B. M.; McComas, C. B.; Craft, L. E. Synth. Commun. 2005, 35, 663.
- (2005) Synth. Commun , vol.35 , pp. 663
- DiCesare, J.C.¹ White, C.E.² Rasmussen, W.E.³ White, B.M.⁴ McComas, C.B.⁵ Craft, L.E.⁶

13
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- (d) Groth, T.; Grötli, M.; Lubell, W. D.; Miranda, L. P.; Meldal, M. J. Chem. Soc., Perkin Trans. 1 2000, 4258.
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- Groth, T.¹ Grötli, M.² Lubell, W.D.³ Miranda, L.P.⁴ Meldal, M.⁵

14
- 38849196420
- Spectroscopic data for 12c: 1H NMR (300 MHz, CDCl 3, δ, 3.02 (s, 6 H, NMe2, 5.79 (s, 2 H, CH 2, 7.12 (br d, 3J, 8.67 Hz, 2 H, 3′-H, 5′-H, 7.30 (br d, 3J, 8.67 Hz, 2 H, 2′-H, 6′-H, 7.32-7.45 (m, 3 H, 5-H, 6-H, 7-H, 8.05 (ddd, 3J, 8.10 Hz, 4J, 1.13 Hz, 5J, 0.94 Hz, 1 H, 4-H, 13C NMR (75 MHz, CDCl3, δ, 43.5, NMe, 51.7, CH2, 109.6, CAr, 117.3, 2 x C, CAr′, 119.9, CAr, 124.3, CAr, 127.7, CAr, 129.3, 2 x C, CAr′, 129.9 (quart, C-7a, 132.7 (quart, C-1′, 145.9 (quart, C-4′, 146.8 quart, C-3a
- 2), 109.6 (+, CAr), 117.3 (+, 2 x C, CAr′), 119.9 (+, CAr), 124.3 (+, CAr), 127.7 (+, CAr), 129.3 (+, 2 x C, CAr′), 129.9 (quart, C-7a), 132.7 (quart, C-1′), 145.9 (quart, C-4′), 146.8 (quart, C-3a).

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