Name: preparation of n-(2-alkoxyvinyl)sulfonamides from n-tosyl-1,2,3-triazoles and subsequent conversion to substituted phthalans and phenethylamines
Uploaded: 2018-01-03T15:00:00
Description: Watch this Scientific Journal Video about Preparation of N-2-alkoxyvinylsulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines at JoVE.com

यह काम हैमिल्टन कॉलेज द्वारा वित्त पोषित किया गया और एडवर्ड और वर्जीनिया टेलर कोष के छात्र के लिए रसायन विज्ञान में अनुसंधान/

1. N-Tosyl Triazole 2a का संश्लेषण: (2-(1-Tosyl-1एच-1, 2, 3-triazol-4-yl) फिनाइल) मेथनॉल
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	<li>एक 3 एक्स 10 मिमी PTFE चुंबकीय हलचल पट्टी, १३९ मिलीग्राम 2-ethynylbenzyl शराब, और तांबे की 20 मिलीग्राम (I) thiophenecarboxylate (CuTC) एक ओवन सूखे 2-5 मिलीलीटर माइक्रोवेव शीशी ...

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Triazoles 2a-b एक घन (I)-catalyzed azide-alkyne [3 + 2] cycloaddition (CuAAC) उत्प्रेरक के रूप में CuTC का उपयोग कर के माध्यम से साफ रूप से प्राप्त किया जा सकता है । विशेष रूप से, triazole 2a सबसे कुशलतापूर्वक 3h या हीटिंग के लिए १०० डिग्री सेल्सि?...

रोडियाम (II)-azavinyl carbenoids हाल ही में कई मूल्यवान उत्पादों के लिए एक असाधारण बहुमुखी प्रतिक्रियाशील मध्यवर्ती एन मार्ग के रूप में उभरा है । 1 , 2 , 3 , 4 , 5 , ६ , 7 , 8 , 9 , 10 विशेष रूप से, heterocycles10 के उत्पादन के लिए इन मध्यवर्ती के कई उपंयास उपयोगों नए और कुशल सिंथेटिक रणनीतियों के साथ दवा प्रदान की है । इस अंत की ओर, हमारे समूह phthalans11 के संश्लेषण के लिए एक नए प्रोटोकॉल के विकास की शुरुआत की है कि अंतर में हाल ही में प्रगति पर कैपिटल होगा और ऑक्सीजन के intramolecular जोड़-आरएच को nucleophiles आधारित (द्वितीय)-azavinyl carbenoids N-sulfonyl-1, 2, 3-triazoles से व्युत्पंन । 12 , 13 , 14 , 15 , 16 , 17 हमारे दृष्टिकोण ऐसे 1 में N-sulfonyl-1, 2, 3-triazoles 2 एक pendent शराब असर (चित्रा 1) के रूप में टर्मिनल alkynes परिवर्तित करने के लिए एक सरल दो कदम प्रोटोकॉल सुविधाएं । इसके बाद, एक आरएच (द्वितीय)-catalyzed (2-alkoxyvinyl) 1, 3-ओह सम्मिलन झरना 2 से प्रदान करता है phthalans 3 एक प्रतिक्रियाशील एन-(२) sulfonamide कार्यात्मक समूह ।
के बाद से एन-(2-alkoxyvinyl) sulfonamide moiety एक संभावित बहुमुखी है, लेकिन अपेक्षाकृत बेरोज़गार एनऔर ओयुक्त synthon,16,17,18, 19 , 20 , 21 , 22 , 23 , 24 , 25 , 26 , 27 हम स्थितियों की एक किस्म (चित्रा 2) के तहत अपने जुड़े enol-ईथर की प्रतिक्रिया का अध्ययन करने में रुचि हो गई/ विभिंन कम करने प्रोटोकॉल स्क्रीनिंग के बाद, दो तरीकों की पहचान की है जो स्थिर phthalan और/या phenethylamine युक्त उत्पादों (चित्रा 2, 3 → 4/ सबसे पहले, यह पता चला था कि एनके एक मानक हाइड्रोजन-(2-alkoxyvinyl) कार्बन पर उत्प्रेरक पैलेडियम के साथ sulfonamide 3 ए (पीडी/चुनिंदा सी = सी बंधन को कम कर देता है phthalan 4उपज । वैकल्पिक रूप से, सोडियम बीआईएस के साथ 3 ए के उपचार (2-methoxyethoxy) एल्यूमीनियम hydride diethyl ईथर में/टोल्यूनि प्रदान करता है विशिष्ट प्रतिस्थापित phenethylamine व्युत्पंन 5। हम मानते है कि इन परिवर्तनों के दोनों मूल्यवान हैं, क्योंकि वे neuroactive एंबेडेड phenethylamine से उत्पंन गुणों सहित संभावित जैविक गतिविधि के साथ उत्पाद वर्गों के लिए सीसा, और 4के मामले में, धातु-केलेशनथेरेपी के माध्यम से सीआईएसउंमुख एनऔर ओ-परमाणुओं ।
हालांकि एसिड की जांच के लिए इलेक्ट्रॉन-रिच सी = 3के सी बांड का फायदा उठाने संवर्धित, यह पाया गया कि शराब या एक thiol की उपस्थिति में उत्प्रेरक trimethylsilyl क्लोराइड के साथ इस परिसर का उपचार ketals 6a-सी और bicyclic phthalan ढांचा बरकरार रखते हुए क्रमशः thioketal 6e. वैकल्पिक रूप से, एक 1:1 एसिटिक एसिड में 3 ए उभार/पानी समाधान पैदावार स्थिर hemiketal 6d।

<table border="0" cellpadding="0" cellspacing="0" width="829">
	<tbody>
		<tr height="21">
			<td height="21" style="height:21px;width:324px;">2-Ethynylbenzyl alcohol, 95%</td>
			<td style="width:219px;">Sigma Aldrich</td>
			<td style="width:119px;">520039</td>
			<td style="width:167px;"></td>
		</tr>
		<tr height="21">
			<td height="21" style="height:21px;width:324px;">Copper (I) thiophene-2-carboxylate</td>
			<td style="width:219px;">Sigma Aldrich</td>
			<td style="width:119px;">682500</td>
			<td></td>
		</tr>
		<tr height="21">
			<td height="21" style="height:21px;width:324px;">Chloroform, &#8805;99%</td>
			<td style="width:219px;">Sigma Aldrich</td>
			<td style="width:119px;">372978</td>
			<td></td>
		</tr>
		<tr height="21">
			<td height="21" style="height:21px;width:324px;">Toluenesulfonylazide, 99.24%</td>
			<td style="width:219px;">Chem-Impex International</td>
			<td style="width:119px;">26107</td>
			<td>Potentially explosive</td>
		</tr>
		<tr height="21">
			<td height="21" style="height:21px;width:324px;">Dichloromethane, &#8805;99.5%</td>
			<td style="width:219px;">Sigma Aldrich</td>
			<td style="width:119px;">320269</td>
			<td></td>
		</tr>
		<tr height="21">
			<td height="21" style="height:21px;width:324px;">Rhodium (II) acetate dimer, 99%</td>
			<td style="width:219px;">Strem Chemicals</td>
			<td style="width:119px;">45-1730</td>
			<td></td>
		</tr>
		<tr height="21">
			<td height="21" style="height:21px;width:324px;">Silica Gel, 32-63, 60A</td>
			<td style="width:219px;">MP Biomedicals Inc.</td>
			<td style="width:119px;">2826</td>
			<td>For silica gel plugs</td>
		</tr>
		<tr height="21">
			<td height="21" style="height:21px;width:324px;">Hexanes</td>
			<td style="width:219px;">Sigma Aldrich</td>
			<td style="width:119px;">178918</td>
			<td></td>
		</tr>
		<tr height="21">
			<td height="21" style="height:21px;width:324px;">Ethyl acetate</td>
			<td style="width:219px;">Sigma Aldrich</td>
			<td style="width:119px;">439169</td>
			<td></td>
		</tr>
		<tr height="21">
			<td height="21" style="height:21px;width:324px;">Chlorofom-D</td>
			<td style="width:219px;">Sigma Aldrich</td>
			<td style="width:119px;">151823</td>
			<td></td>
		</tr>
		<tr height="21">
			<td height="21" style="height:21px;width:324px;">Ethylene glycol</td>
			<td style="width:219px;">Sigma Aldrich</td>
			<td style="width:119px;">293237</td>
			<td></td>
		</tr>
		<tr height="21">
			<td height="21" style="height:21px;width:324px;">Chlorotrimethylsilane, 98%</td>
			<td style="width:219px;">Acros</td>
			<td style="width:119px;">11012</td>
			<td></td>
		</tr>
		<tr height="21">
			<td height="21" style="height:21px;width:324px;">Sodium bicarbonate</td>
			<td style="width:219px;">Sigma Aldrich</td>
			<td style="width:119px;">S6014</td>
			<td>Dissolved in deionized water to prepare a saturated aqueous solution</td>
		</tr>
		<tr height="21">
			<td height="21" style="height:21px;width:324px;">Sodium sulfate</td>
			<td style="width:219px;">Fisher Scientific</td>
			<td style="width:119px;">S429</td>
			<td></td>
		</tr>
		<tr height="21">
			<td height="21" style="height:21px;width:324px;">Ethyl alcohol, absolute - 200 proof</td>
			<td style="width:219px;">Aaper Alcohol and Chemical Co.</td>
			<td style="width:119px;">82304</td>
			<td></td>
		</tr>
		<tr height="21">
			<td height="21" style="height:21px;width:324px;">10 wt% Palladium on carbon</td>
			<td style="width:219px;">Sigma Aldrich</td>
			<td style="width:119px;">520888</td>
			<td>Can ignite in the presence of air, hydrogen gas, and/or a flammable solvent</td>
		</tr>
		<tr height="21">
			<td height="21" style="height:21px;width:324px;">Hydrogen gas</td>
			<td style="width:219px;">Praxair</td>
			<td style="width:119px;">UN1049</td>
			<td></td>
		</tr>
		<tr height="21">
			<td height="21" style="height:21px;width:324px;">Diethyl ether</td>
			<td style="width:219px;">Sigma Aldrich</td>
			<td style="width:119px;">309966</td>
			<td></td>
		</tr>
		<tr height="42">
			<td height="42" style="height:42px;width:324px;">60 wt% sodium bis(2-methoxyethoxy)aluminum hydride solution in toluene</td>
			<td style="width:219px;">Sigma Aldrich</td>
			<td style="width:119px;">196193</td>
			<td>Reacts violently with water</td>
		</tr>
		<tr height="21">
			<td height="21" style="height:21px;width:324px;">Methanol</td>
			<td style="width:219px;">Sigma Aldrich</td>
			<td style="width:119px;">34966</td>
			<td></td>
		</tr>
		<tr height="21">
			<td height="21" style="height:21px;width:324px;">Ammonium chloride</td>
			<td style="width:219px;">Fisher Scientific</td>
			<td style="width:119px;">A661</td>
			<td>Dissolved in deionized water to prepare a saturated aqueous solution</td>
		</tr>
		<tr height="21">
			<td height="21" style="height:21px;width:324px;">Hydrochloric acid, 37%</td>
			<td style="width:219px;">Sigma Aldrich</td>
			<td style="width:119px;">258148</td>
			<td>Dissolved in deionized water to prepare a 1M solution</td>
		</tr>
		<tr height="21">
			<td height="21" style="height:21px;width:324px;">Sodium Chloride</td>
			<td style="width:219px;">Sigma Aldrich</td>
			<td style="width:119px;">S25541</td>
			<td>Dissolved in deionized water to prepare a saturated aqueous solution</td>
		</tr>
		<tr height="21">
			<td height="21" style="height:21px;width:324px;">2-5 mL Microwave vials</td>
			<td style="width:219px;">Biotage</td>
			<td style="width:119px;">355630</td>
			<td></td>
		</tr>
		<tr height="21">
			<td height="21" style="height:21px;width:324px;">Microwave vial caps</td>
			<td style="width:219px;">Biotage</td>
			<td style="width:119px;">352298</td>
			<td></td>
		</tr>
		<tr height="42">
			<td height="42" style="height:42px;width:324px;">RediSep Rf Gold Normal Phase, Silica Columns, 20 &#8211; 40 micron</td>
			<td style="width:219px;">Teledyne Isco</td>
			<td style="width:119px;">69-2203-345</td>
			<td>For column chromatography</td>
		</tr>
		<tr height="21">
			<td height="21" style="height:21px;width:324px;">Balloons</td>
			<td style="width:219px;">CTI Industries Corp.</td>
			<td style="width:119px;">912100</td>
			<td>For hydrogenation</td>
		</tr>
		<tr height="21">
			<td height="21" style="height:21px;width:324px;">Biotage Initiator+ Microwave Reactor</td>
			<td style="width:219px;">Biotage</td>
			<td style="width:119px;">356007</td>
			<td></td>
		</tr>
	</tbody>
</table>

preparation of n-(2-alkoxyvinyl)sulfonamides from n-tosyl-1,2,3-triazoles and subsequent conversion to substituted phthalans and phenethylamines

N-tosyl के अपघटन-1, 2, 3-triazoles रोडियाम के साथ (II) शराबियों की उपस्थिति में एसीटेट डिमर कृत्रिम रूप से बहुमुखी n-(2-alkoxyvinyl) सल्फोनामाइड, जो शर्तों की एक किस्म के तहत प्रतिक्रिया करने के लिए उपयोगी वहन एन- और ओ-युक्त यौगिकों । अम्ल-catalyzed के अलावा अल्कोहल या thiols को N-(2-alkoxyvinyl) sulfonamide-युक्त phthalans क्रमशः ketals और thioketals तक पहुंच प्रदान करता है । N-(2-alkoxyvinyl) में vinyl समूह की चयनात्मक कमी sulfonamide-हाइड्रोजन के माध्यम से युक्त phthalans पैदावार अच्छी उपज में इसी phthalan, जबकि सोडियम बीआईएस के साथ कमी (2-methoxyethoxy) aluminumhydride एक उत्पंन रिंग-खोला phenethylamine एनालॉग । क्योंकि N-(2-alkoxyvinyl) sulfonamide कार्यात्मक समूह कृत्रिम रूप से बहुमुखी है, लेकिन अक्सर अस्थिर hydrolytically, इस प्रोटोकॉल की तैयारी में महत्वपूर्ण तकनीकों पर जोर देती है, हैंडलिंग, और कई उपयोगी में इन निर्णायक सब्सट्रेट प्रतिक्रिया परिवर्तनों.

इस अध्ययन में सभी यौगिकों 1एच और 13सी एनएमआर स्पेक्ट्रोस्कोपी और electrospray ionization मास स्पेक्ट्रोमेट्री (ईएसआई-एमएस) उत्पाद संरचना की पुष्टि करने और शुद्धता का आकलन करने के लिए की विशेषता थ?...

Watch this Scientific Journal Video about Preparation of N-2-alkoxyvinylsulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines at JoVE.com

Preparation of N-2-alkoxyvinylsulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines

n-(2-alkoxyvinyl) सल्फोनामाइड की तैयारी n-tosyl-1, 2, 3-triazoles और बाद में स्थानापन्न Phthalans और Phenethylamines के लिए रूपांतरण

प्रतिनिधि के संश्लेषण के लिए प्रायोगिक प्रक्रियाओं N-(2-alkoxyvinyl) सल्फोनामाइड और phthalan और phenethylamine डेरिवेटिव के बाद रूपांतरण विस्तार से प्रस्तुत कर रहे हैं ।

Decomposition of N-tosyl-1,2,3-triazoles with rhodium(II) acetate dimer in the presence of alcohols forms synthetically versatile ...

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Preparation of N-(2-alkoxyvinyl)sulfonamides from N-tosyl-1,2,3-triazoles and Subsequent Conversion to Substituted Phthalans and Phenethylamines

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