Synthesis of 2-aminothiazoles from styrene derivatives mediated by 1,3-dibromo-5,5-dimethylhydrantoin (DBH)

Ma, Chunhua; Miao, Yuqi; Zhao, Mengjuan; Wu, Ping; Zhou, Jiaqi; Li, Zhi; Zhang, Wei

doi:10.1016/j.tet.2018.05.021

Cited by 9 publications

(8 citation statements)

References 33 publications

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“…4‐( p ‐Tolyl)thiazol‐2‐amine (3ba) : [ 18 ] Chemical Formula: C 10 H 10 N 2 S; Appearance: White Solid; Yield: 40 mg (42%); MP: 128°C to 130°C (lit. 124°C‐126°C) [ 18 ] ; FT‐IR (neat): 3452, 3297, 3117, 2757, 1634, 1537, 1331, 1035, 1 H NMR (CDCl 3 , 500 MHz) δ 7.67 (d, J = 8.0 Hz, 2H), 7.19 (d, J = 8.0 Hz, 2H), 6.67 (s, 1H), 5.02 (s, 2H), 2.36 (s, 3H); 13 C NMR (CDCl 3 , 125 MHz) δ 167.2, 151.6.…”

Section: Methodsmentioning

confidence: 99%

“…4-Phenylthiazol-2-amine (3aa): [17] Chemical Formula: C 9 H 8 N 2 S; Appearance: White Solid; Yield: 51 mg (58%); MP: 150 C to 152 C (lit. 151 C-153 C) [17] 4-(p-Tolyl)thiazol-2-amine (3ba): [18] Chemical Formula: C 10 H 10 N 2 S; Appearance: White Solid; Yield: 40 mg (42%); MP: 128 C to 130 C (lit. 124 C-126 C) [18] ; FT-IR (neat): 3452, 3297, 3117, 2757, 1634, 1537, 1331, 1035, 4-(m-Tolyl)thiazol-2-amine (3ca): [17] Chemical Formula: C 10 H 10 N 2 S; Appearance: White Solid; Yield: 39 mg (41%); MP: 84 C to 86 C (lit.…”

Section: Compound Characterization Datamentioning

confidence: 99%

“…151 C-153 C) [17] 4-(p-Tolyl)thiazol-2-amine (3ba): [18] Chemical Formula: C 10 H 10 N 2 S; Appearance: White Solid; Yield: 40 mg (42%); MP: 128 C to 130 C (lit. 124 C-126 C) [18] ; FT-IR (neat): 3452, 3297, 3117, 2757, 1634, 1537, 1331, 1035, 4-(m-Tolyl)thiazol-2-amine (3ca): [17] Chemical Formula: C 10 H 10 N 2 S; Appearance: White Solid; Yield: 39 mg (41%); MP: 84 C to 86 C (lit. 88 C-91 C) [17] ; H NMR (DMSO-d6, 500 MHz) δ 8.71 (bs, 2H), 7.55 (s, 1H), 7.51 (d, J = 10.0 Hz, 1H), 7.29 (t, J = 7.5 Hz, 1H), 7.17 (d, J = 7.5 Hz, 1H), 7.13 (s, 1H), 2.29 (s, 3H); 13 4-(4-Chlorophenyl)thiazol-2-amine (3da): [17] Chemical Formula: C 9 H 7 ClN 2 S; Appearance: White Solid; Yield: 64 mg (61%); MP: 165 C to 167 C (lit.…”

Section: Compound Characterization Datamentioning

confidence: 99%

“…88 C-91 C) [17] ; H NMR (DMSO-d6, 500 MHz) δ 8.71 (bs, 2H), 7.55 (s, 1H), 7.51 (d, J = 10.0 Hz, 1H), 7.29 (t, J = 7.5 Hz, 1H), 7.17 (d, J = 7.5 Hz, 1H), 7.13 (s, 1H), 2.29 (s, 3H); 13 4-(4-Chlorophenyl)thiazol-2-amine (3da): [17] Chemical Formula: C 9 H 7 ClN 2 S; Appearance: White Solid; Yield: 64 mg (61%); MP: 165 C to 167 C (lit. 161 C-162 C) [17] ; FT-IR (neat): 3435, 3279, 3108, 2757, 1631, 1532, 1327, 1036, 4-(3-Chlorophenyl)thiazol-2-amine (3ea): [18] Chemical Formula: C 9 H 7 ClN 2 S; Appearance: White Solid; Yield: 58 mg (55%); MP: 128 C to 130 C (lit. 126 C-128 C) [18] ; FT-IR (neat): 3310, 3127, 1632, 1517, 1337, 1050, 1 4-(2,4-Dichlorophenyl)thiazol-2-amine (3fa): [19] Chemical Formula: C 9 H 6 Cl 2 N 2 S; Appearance: White Solid; Yield: 61 mg (50%); MP: 157 C to 159 C (lit.…”

Section: Compound Characterization Datamentioning

confidence: 99%

“…179 C-181 C) [18] ; FT-IR (neat): 3426, 3279, 3109, 2757, 1634, 1531, 1334, 1035, 4-(4-Fluorophenyl)thiazol-2-amine (3ia): [18] Chemical Formula: C 9 H 7 FN 2 S; Appearance: White Solid; Yield: 53 mg (55%); MP: 100 C to 102 C (lit. 103 C-104 C) [18] ;…”

Section: Compound Characterization Datamentioning

confidence: 99%

See 4 more Smart Citations

Novel synthesis of 2‐Aminothiazoles via Fe(III)‐Iodine‐catalyzed Hantzsch‐type condensation

Ujwaldev

Harry

Neetha

et al. 2020

Journal of Heterocyclic Chem

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A novel iron‐iodine catalyzed one pot synthesis of 2‐aminothiazoles from methyl aryl ketones and thiourea is demonstrated. This protocol can be considered as a catalyzed version of the classical Hantzsch aminothiazole synthesis as it enables the in situ generation of α‐iodoketones in the reaction medium using catalytic amount of iodine leading to Hantzsch condensation with thiourea. The supply of iodine for multiple catalytic cycles is ensured by using catalytic amounts of iron as it enables iodide to iodine oxidation. The generality of this protocol is also well established in this manuscript by synthesizing a variety of 2‐aminothiazoles from different ketones and thiourea.

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Section: Methodsmentioning

confidence: 99%

Section: Compound Characterization Datamentioning

confidence: 99%

Section: Compound Characterization Datamentioning

confidence: 99%

Section: Compound Characterization Datamentioning

confidence: 99%

Section: Compound Characterization Datamentioning

confidence: 99%

See 3 more Smart Citations

Novel synthesis of 2‐Aminothiazoles via Fe(III)‐Iodine‐catalyzed Hantzsch‐type condensation

Ujwaldev

Harry

Neetha

et al. 2020

Journal of Heterocyclic Chem

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2‐Amino‐4‐arylthiazoles through One‐Pot Transformation of Alkylarenes with NBS and Thioureas

Shibasaki

Togo

2019

Eur J Org Chem

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Treatment of alkylarenes with N‐bromosuccinimide in a mixture of ethyl acetate and water at 60 °C, a mixture of acetonitrile and water at 80 °C, or a mixture of diethyl carbonate and water under irradiation with a tungsten lamp, followed by a reaction with thioureas or arenethioamides provided the corresponding 2‐amino‐ 4‐arylthiazoles or 2,4‐diarylthiazoles in good to moderate yields, respectively, in one pot. The present reaction is an efficient one‐pot transformation method of alkylarenes into 2‐amino‐4‐arylthiazoles and 2,4‐diarylthiazoles directly under mild and transition‐metal‐free conditions.

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An efficient one-pot synthesis of 2-aminothiazoles via electrochemically oxidative α-C-H functionalization of ketones with thioureas

Yang

Fang

et al. 2022

Journal of Environmental Chemical Engineering

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Synthesis of 2-aminothiazoles from styrene derivatives mediated by 1,3-dibromo-5,5-dimethylhydrantoin (DBH)

Cited by 9 publications

References 33 publications

Novel synthesis of 2‐Aminothiazoles via Fe(III)‐Iodine‐catalyzed Hantzsch‐type condensation

Novel synthesis of 2‐Aminothiazoles via Fe(III)‐Iodine‐catalyzed Hantzsch‐type condensation

2‐Amino‐4‐arylthiazoles through One‐Pot Transformation of Alkylarenes with NBS and Thioureas

An efficient one-pot synthesis of 2-aminothiazoles via electrochemically oxidative α-C-H functionalization of ketones with thioureas

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