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1 article(s) from Hosseinzadeh-Khanmiri, R.

N-Propargylamines: versatile building blocks in the construction of thiazole cores

S. Arshadi,
E. Vessally,
L. Edjlali,
R. Hosseinzadeh-Khanmiri and
E. Ghorbani-Kalhor

Beilstein J. Org. Chem. 2017, 13, 625–638, doi:10.3762/bjoc.13.61

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Graphical Abstract

Figure 1: Selected examples of bioactive thiazole derivatives.

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Figure 2: Some natural sources of thiazoles.

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Figure 3: Some important thiazole-based compounds derived from N-propargylamines.

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Scheme 1: The synthesis of thiazole-2-thiones 3 through the thermal cyclocondensation of N-propargylamines 1 ...

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Scheme 2: (a) One-pot synthesis of 2-benzylthiazolo[3,2-a]benzimidazoles 6 through a base-catalyzed cascade r...

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Scheme 3: (a) Synthesis of 2-iminothiazolidines 11 from N-propargylamines 9 and isothiocyanates 10. (b) Synth...

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Scheme 4: (a) Synthesis of 2-aminothiazoles 17 through the reaction of ethyl 4-aminobut-2-ynoate salts 15 wit...

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Scheme 5: Synthesis of 5-(iodomethylene)-3-methylthiazolidines 27 described by Zhou.

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Scheme 6: Mechanism that accounts for the formation of 27.

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Scheme 7: Clausen’s synthesis of fluorescein thiazolidines 30.

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Scheme 8: Synthesis of multiply substituted thiazolidines 33 from N-propargylamines 32 and blocked N-isothioc...

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Scheme 9: (a) Microwave-assisted cyclization of N-propargyl thiocarbamate 34. (b) Synthesis of thiazoles 39 t...

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Scheme 10: Synthesis of thiazolidines 42 (42’) from the reaction of β-oxodithioesters 40 (40’) with N-propargy...

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Scheme 11: Synthesis of 5-(dibromomethyl)thiazoles 44 via halocyclization of N-propargylamines 43 described by...

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Scheme 12: Synthesis of dihydrothiazoles 46 through the treatment of N-propargylamides 45 with Lawesson’s reag...

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Scheme 13: Synthesis of thiazoles 49 by treatment of silyl-protected N-propargylamines 47 with benzotriazolylt...

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Scheme 14: Mechanism proposed to explain the synthesis of 2,5-disubstituted thiazoles 49 developed by Sasmal.

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Scheme 15: Mo-catalyzed cyclization of N-propargylthiocarbamate 50.

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Scheme 16: (a) DABCO-mediated intramolecular cyclization of N-(propargylcarbamothioyl)amides 53 to the corresp...

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Scheme 17: Proposed mechanism for the generation of the iodine-substituted 4H-1,3-thiazines 56 and 4,5-dihydro...

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Scheme 18: Au(III)-catalyzed synthesis of 5-alkylidenedihydrothiazoles 58 developed by Stevens.

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Review

Published 30 Mar 2017

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