Name: protocol for the synthesis of ortho-trifluoromethoxylated aniline derivatives
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ونحن نعترف أموال لبدء سخية من جامعة ولاية نيويورك في ستوني بروك في دعم هذا العمل. كما نشكر TOSOH F-تك، شركة لتزويدنا TMSCF 3 كاشف لتركيب Togni الكاشف الثاني.

1. السلائف التحضير: توليف الميثيل 4- (N -hydroxyacetamido) بنزوات (1A) <ol style=";text-align:right;direction:rtl"><li style=";text-align:right;direction:rtl"> تخفيض الميثيل 4-nitrobenzoate. <ol style=";text-align:right;direction:rtl"><li style=";text-align:right;direction:rtl"> إضافة 5.00 غرام من الميثيل 4-nitrobenzoate (27.6 مليمول، 1.00 EQUIV)، 159 ملغ من 5٪ الروديوم ...

<ol>
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ونظرا لعدم وجود إجراء عام وسهلة الاستعمال لتركيب أرينية trifluoromethoxylated، العديد من OCF 3 المحتوية على المركبات العطرية هي مكلفة للغاية. 34 استراتيجيتنا إزاحة التسامح مجموعة وظيفية واسعة ويوفر سهولة الوصول إلى مختلف أرينية trifluoromethoxylated. هذه المركبات يمكن أن تكون...

وtrifluoromethoxy جعلت (OCF 3) مجموعة لها تأثير عميق على البحوث الحياة وعلوم المواد منذ التوليف الأول من الأثير ترايفلوروميثيل في عام 1935. 2 نظرا لمزيج فريد من كهربية عالية (χ = 3.7) 3 وبالانجذاب ممتاز (Π س = وقد وجدت 1.04)، 4 مجموعة trifluoromethoxy تطبيقات واسعة في مجال الطب، والزراعة، وصناعة مواد 5-10 ومع ذلك، لا يزال مقدمة سطحي من مجموعة OCF 3 في الجزيئات العضوية، وخاصة المركبات العطرية، تحديا كبيرا في الكيمياء الاصطناعية. على مدى العقود القليلة الماضية، أدت الجهود لمواجهة هذا التحدي في تطوير حفنة من التحولات لتركيب أرينية trifluoromethoxylated 5-7،9-11 هذه تشمل (ط) تبادل الكلور / الفلور على السلائف trichlorinated؛ 1،12 -17 (ب) deoxyfluorination من fluoroformates (18)؛ </سوب&gt; (ج) fluorodesulfurization الأكسدة، 19-21 (د) trifluoromethylation أليف الإلكترونات من الكحول، 22-25 (V) trifluoromethoxylation أليف النواة، 26-30، (السادس) الانتقال بوساطة المعادن trifluoromethoxylation من بورات أريل وstannanes (31)؛ و (السابع ) trifluoromethoxylation راديكالية. 32،33 ومع ذلك، فإن العديد من هذه الطرق إما يعانون من سوء نطاق الركيزة أو تتطلب استخدام الكواشف شديدة السمية و / أو عطوب حراريا. لذلك، نظرا لعدم وجود طريقة عامة وسهلة الاستعمال لتجميع OCF 3 مركبات فيتامين، وإمكانات مجموعة OCF 3 لم تستغل بالكامل في الكيمياء. كجزء من مصلحتنا في التفاعلات trifluoromethoxylation، 34 وصفنا هنا بروتوكول من خطوتين (أي O راديكالية -trifluoromethylation وOCF التي يسببها حراريا 3 -migration) لتركيب الميثيل 4-acetamido-3- (trifluoromethoxy) بنزوات (3A) من الميثيل 4- (N -hydroxyacetamido) بنزوات (1A). الاستراتيجية هي سهلة لتشغيل وتنطبق على تركيب مجموعة واسعة من أورثو مشتقات الأنيلين -trifluoromethoxylated.

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	<tbody>
		<tr height="43">
			<td height="43" style="height:43px;width:216px;">5% Rhodium on carbon</td>
			<td style="width:71px;">Aspira Scientific</td>
			<td style="width:119px;">300835</td>
			<td style="width:167px;">5% wt% dry loading</td>
		</tr>
		<tr height="43">
			<td height="43" style="height:43px;width:216px;">hydrazine monohydrate</td>
			<td style="width:71px;">Sigma-Alderich</td>
			<td style="width:119px;">13696HMV</td>
			<td style="width:167px;">Reagent grade, 98%</td>
		</tr>
		<tr height="43">
			<td height="43" style="height:43px;width:216px;">Acetyl chloride</td>
			<td style="width:71px;">Alfa Aesar</td>
			<td style="width:119px;">10176887</td>
			<td style="width:167px;">98%</td>
		</tr>
		<tr height="43">
			<td height="43" style="height:43px;width:216px;">Sodium bicarbonate</td>
			<td style="width:71px;">Fisher Scientific</td>
			<td style="width:119px;">134826</td>
			<td style="width:167px;">Chemical pure</td>
		</tr>
		<tr height="43">
			<td height="43" style="height:43px;width:216px;">Cesium carbonate</td>
			<td style="width:71px;">Alfa Aesar</td>
			<td style="width:119px;">12887</td>
			<td style="width:167px;">99.9%, metals basis</td>
		</tr>
		<tr height="148">
			<td height="148" style="height:148px;width:216px;">Togni Reagent II</td>
			<td style="width:71px;"></td>
			<td style="width:119px;"></td>
			<td style="width:167px;">Prepared according to the literature procedure (ref 37). Caution: Pure Togni reagent II is impact and friction sensitive, treat it with great care (see ref. 36).</td>
		</tr>
		<tr height="64">
			<td height="64" style="height:64px;width:216px;">Tetrahydrofuran</td>
			<td style="width:71px;">BDH</td>
			<td style="width:119px;">BDH1149-4LG</td>
			<td style="width:167px;">Distilled from deep purple sodium benzophenone ketyl.</td>
		</tr>
		<tr height="64">
			<td height="64" style="height:64px;width:216px;">Diethyl Ether</td>
			<td style="width:71px;">Fisher Scientific</td>
			<td style="width:119px;">148221</td>
			<td style="width:167px;">Distilled from deep purple sodium benzophenone ketyl.</td>
		</tr>
		<tr height="47">
			<td height="47" style="height:47px;width:216px;">Chloroform</td>
			<td style="width:71px;">Fisher Scientific</td>
			<td style="width:119px;">141739</td>
			<td style="width:167px;">Dried over CaH2 and distilled</td>
		</tr>
		<tr height="47">
			<td height="47" style="height:47px;width:216px;">nitro methane</td>
			<td style="width:71px;">Alfa Aesar</td>
			<td style="width:119px;">J03z053</td>
			<td style="width:167px;">Dried over CaSO4 and distilled</td>
		</tr>
		<tr height="43">
			<td height="43" style="height:43px;width:216px;">Silica gel</td>
			<td style="width:71px;">SILICYCLE</td>
			<td style="width:119px;">60514</td>
			<td style="width:167px;">40-63 &#181;m (230-400 mesh)</td>
		</tr>
		<tr height="22">
			<td height="22" style="height:22px;width:216px;">Cilite</td>
			<td style="width:71px;">EMD</td>
			<td style="width:119px;">2012040674</td>
			<td style="width:167px;">Not acid washed</td>
		</tr>
	</tbody>
</table>

protocol for the synthesis of ortho-trifluoromethoxylated aniline derivatives

جزيئات تحمل trifluoromethoxy (OCF 3) مجموعة غالبا ما تظهر المطلوب الخصائص الدوائية والبيولوجية. ومع ذلك، والتوليف سطحي من المركبات العطرية trifluoromethoxylated لا يزال يشكل تحديا هائلا في التركيب العضوي. وغالبا ما تعاني الأساليب التقليدية من سوء نطاق الركيزة، أو تتطلب استخدام عالية السمية، والتعامل مع يصعب، و / أو الكواشف عطوب حراريا. هنا، ونحن التقرير بروتوكول سهل الاستعمال لتركيب الميثيل 4-acetamido-3- (trifluoromethoxy) بنزوات باستخدام 1-ترايفلوروميثيل-1،2-benziodoxol-3 (1 H) واحد (Togni كاشف II). علاج الميثيل 4- (N -hydroxyacetamido) بنزوات (1A) مع Togni الكاشف الثاني في وجود كمية الحفاز من السيزيوم كربونات (CS 2 3 CO) في الكلوروفورم في RT تمنح الميثيل 4- (N - (trifluoromethoxy) acetamido) بنزوات (2A). هذا المتوسط ​​ثم تم تحويلها إلى الميثيل المنتج النهائي 4-acetamido-3- (trifluoromethoxy) بنزوات (3A) في النيتروميثان في 120 ° C. هذا الإجراء هو عام ويمكن تطبيقها على تركيب مجموعة واسعة من أورثو مشتقات الأنيلين -trifluoromethoxylated، والتي يمكن أن تكون مفيدة لبنات البناء الاصطناعية لاكتشاف وتطوير الأدوية الجديدة والكيماويات الزراعية، والمواد الفنية.

تم توليفها الميثيل 4- (N -hydroxyacetamido) بنزوات (1A) في العائد معزولة 92٪ من خلال إجراء خطوتين (أي الحد الميثيل 4-nitrobenzoate مع الهيدرازين باستخدام 5٪ ره / C كمحفز لتشكيل الميثيل 4- ( N -hydroxyamino) بنزوات، تليها حماية الاسيتيل من هيدروكسيل الناتج). ...

Watch this Scientific Journal Video about Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives at JoVE.com

Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

بروتوكول لتوليف<em&gt; أورثو</em&gt; مشتقات الانيلين -trifluoromethoxylated

An operationally simple procedure for the synthesis of ortho-trifluoromethoxylated aniline derivatives via a two-step sequence of O-trifluoromethylation of N-aryl-N-hydroxyacetamide followed by thermally induced intramolecular OCF3-migration is reported.

Molecules bearing trifluoromethoxy (OCF3) group often show desired pharmacological and biological properties. However, facile synthesis of ...

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Protocol for the Synthesis of Ortho-trifluoromethoxylated Aniline Derivatives

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