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

이 작품은 해밀턴 대학 에드워드와 화학에 있는 학생/교수 연구에 대 한 버지니아 테일러 기금에 의해 투자 되었다.

1. N-토실기 Triazole 2a의 합성: (2-(1-토실기-1H-1,2,3-triazol-4-yl) 페 닐) 메탄올
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	<li>오븐 건조 2-5 mL 전자 레인지 유리병에 3 x 10 m m PTFE 자기 저 어 바, 2 ethynylbenzyl 알코올의 139 mg 및 copper(I) thiophenecarboxylate (CuTC)의 20 밀리 그램을 추가 하 고 심장 모자와 뇌관 집게 안전 하 게 유리병 밀봉. 전자 레인지의 급속 한 난방으로 인해 항상 새로운 유리병과 모자는 어떤의 사용 하 고 모자는 안전 ...

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Cu (I) 통해 triazoles 2a-b 를 청결 하 게 얻어질 수 있다-아 지 드-alkyne [3 + 2] cycloaddition (CuAAC) CuTC를 사용 하 여 촉매 촉매. 특히, triazole 2a 는 가장 효율적으로 3 h 또는 전자 레인지 원자로 (참고 시간 전자 레인지 효율에 따라 다를 수 있습니다);에서 15 분 100 ° C에 난방에 대 한 클로 프롬에 표준 환류를 통해 고온에서 생성 된 그러나, triazole 2b 는 가장 효율적으로 ?...

로 듐 (II)-azavinyl carbenoids 최근 매우 다양 한 반응 중간 도중에 수많은 귀중 한 제품으로 등장 했습니다. 1 , 2 , 3 , 4 , 5 , 6 , 7 , 8 , 9 , 10 특히, heterocycles10 의 생산에 대 한 이러한 중간체의 많은 소설 사용 제공 새롭고 효율적인 합성 전략 화학자. 이 끝으로 우리의 그룹 간-에 있는 최근 전진에 투자 것 phthalans11 의 합성 및 산소 기반 nucleophiles 하 Rh (II)의 intramolecular 추가 대 한 새로운 프로토콜의 개발 시작-azavinyl carbenoids N에서 파생 된-sulfonyl-1,2,3-triazoles. 12 , 13 , 14 , 15 , 16 , 17 우리의 접근 기능 1 터미널 alkynes N으로 변환 하기 위한 간단한 2 단계 프로토콜-sulfonyl-1,2,3-triazoles 2 베어링 늘어진 알코올 (그림 1). 그 후, 2 차 Rh 촉매 denitrogenation / phthalans 3 데 반응 N을 제공 하는 2 에서 1, 3-오 삽입 캐스케이드-(2-alkoxyvinyl) 술 기능 그룹.
이후 N-(2-alkoxyvinyl) 술 moiety는 잠재적으로 다양, 상대적으로 underexplored N-및 O-synthon,16,,1718, 를 포함 하 19 , 20 , 21 , 22 , 23 , 24 , 25 , 26 , 27 우리는 다양 한 조건 (그림 2)에서 융합된 enol-에테르/한-술 시스템의 반응성을 공부에 관심이 되었다. 다양 한 줄이는 프로토콜 검사, 후 두 가지 방법 안정적인 phthalan 또는 phenethylamine 포함 된 제품에 지도 확인 되었다 (그림 2, 3 → 4/5). 첫째, 그것은 발견 했다 하는 N의 표준 수소-(2-alkoxyvinyl) 촉매 팔라듐에 탄소 (Pd/C)과 술 3a 선택적으로 감소 수익률 phthalan 4C = C 유대. 또는 나트륨 비스 (2-methoxyethoxy) 알루미늄 수 소화물 diethyl 에테르/톨루엔과 3a 의 치료 고유 대체 phenethylamine 파생 5를 제공합니다. 우리는 이러한 변환을 모두 귀중 한, 그들은 잠재적인 생물학적 활동 neuroactive 속성 포함된 phenethylamine에서 그리고 4, 통해 금속 킬레이트의 경우 발생 된 제품 클래스 끌 생각은 cis-지향적인된 N-및 O-원자.
3a의 전자 풍부한 C = C 유대 악용 하 산 승진 추가 조사 하는 동안이 알콜의 존재 촉매 trimethylsilyl 염화 화합물의 그 치료를 발견 했다 나는 thiol 굴복 ketals 6a-c 와 thioketal 6e, bicyclic phthalan 프레임 워크를 그대로 유지 하면서 각각. 또는 1:1 초 산/물 솔루션 수율 안정 hemiketal 6 d에서 3a 을 감동.

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	<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-토실기-1,2,3-triazoles rhodium(II) 아세테이트 이합체 알콜의 존재와 분해 합성으로 다양 한 N형성-(2-alkoxyvinyl) sulfonamides, 다양 한 유용한 N-감당할 조건에서 반응 그리고 O-화합물을 포함 합니다. 알콜 또는 nthiols의 산 촉매 추가-(2-alkoxyvinyl) 술 포함 된 phthalans에 액세스할 ketals와 thioketals, 각각. N에 비닐 그룹의 선택적 감소-(2-alkoxyvinyl) 수소 첨가 통해 술에 포함 된 phthalans 감소 나트륨 비스 (2-methoxyethoxy) aluminumhydride 생성 하는 반면 좋은 수확량에 해당 phthalan 생성 한 링 오픈 phenethylamine 아날로그입니다. 때문에 N-(2-alkoxyvinyl) 술 기능 그룹은 합성으로 다양 한, 하지만 종종 가수분해로 불안정 하 고,이 프로토콜 강조 준비, 처리, 그리고 몇 유용한 이러한 중추적인 기판 반응에 핵심 기술을 변환입니다.

이 연구에서 모든 화합물 1H와 13C NMR 분광학 및 분무 이온화 질량 분석 제품 구조를 확인 하 여 순도 평가 (ESI MS) 특징 이었다. 대표적인 화합물에 대 한 주요 데이터는이 섹션에 설명 되어 있습니다.
스펙트럼 데이터는 2a (그림 3)의 triazole 구조와 좋은 계약에 있습니다. 1</s...

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

N의 준비-(2-alkoxyvinyl) sulfonamides N-토실기-1,2,3-triazoles 및 후속 변환 대체 Phthalans 및 Phenethylamines에서

N의 합성에 대 한 대표적인 실험 절차-(2-alkoxyvinyl) sulfonamides 후속 변환 phthalan와 phenethylamine 파생 상품을 자세히 표시 됩니다.

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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We present herein the optimized synthesis of a triphosphenium bromide salt. Apart from being a versatile metathesis reagent, this unusually stable ...

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