A Novel Transformation of Esters to Alkynes with 1-Substituted Benzotriazoles

AR Katritzky, J Wang, N Karodia…

Index: Katritzky, Alan R.; Wang, Jin; Karodia, Nazira; Li, Jianqing Journal of Organic Chemistry, 1997 , vol. 62, # 12 p. 4142 - 4147

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Citation Number: 32

Abstract

Reactions of lithio benzotriazol-1-yl derivatives 2, 11, and 25 with aromatic and aliphatic esters 3, 12, and 26 gave α-(benzotriazol-1-yl) ketones 4, 13, and 27, respectively, in high yields. Alternatively, α-(benzotriazol-1-yl) ketones 22 can be accessed by the reaction of α- (benzotriazol-1-yl) esters 20 with Grignard reagents. Condensation of 4, 13, 22, and 27 with (p-toluenesulfonyl) hydrazine provided p-tosylhydrazones 5, 14, 21, and 28. Treatment of ...

 Related Synthetic Route
N/A Structure

189343-68-8

N/A

~59%

10-phenyldeca-1,9-diynylbenzene Structure

49769-20-2

10-phenyldeca-1...

1-Benzyl-1H-benzo[d][1,2,3]triazole Structure

4706-43-8

1-Benzyl-1H-ben...

~%

10-phenyldeca-1,9-diynylbenzene Structure

49769-20-2

10-phenyldeca-1...

1,10-bis(1H-benzo[d][1,2,3]triazol-1-yl)-1,10-diphenyldecane-2,9-dione Structure

189343-55-3

1,10-bis(1H-ben...

~%

10-phenyldeca-1,9-diynylbenzene Structure

49769-20-2

10-phenyldeca-1...

METHYLLITHIUM Structure

917-54-4

METHYLLITHIUM

N/A Structure

189343-66-6

N/A

~74%

phenylpropyne Structure

673-32-5

phenylpropyne

METHYLLITHIUM Structure

917-54-4

METHYLLITHIUM

N/A Structure

189343-67-7

N/A

~68%

2-Decyne Structure

2384-70-5

2-Decyne

1-(benzotriazol-1-yl)-2-decanone p-tosylhydrazone Structure

189343-57-5

1-(benzotriazol...

~73%

dec-1-yne Structure

764-93-2

dec-1-yne

N/A Structure

189343-58-6

N/A

~82%

1-Undecyne Structure

2243-98-3

1-Undecyne

Phenyllithium Structure

591-51-5

Phenyllithium

N/A Structure

189343-67-7

N/A

~82%

1-Nonynylbenzene Structure

57718-18-0

1-Nonynylbenzene

2-(benzotriazol-1-yl)-2-phenylacetophenone p-tosylhydrazone Structure

189343-60-0

2-(benzotriazol...

~84%

Diphenylacetylene Structure

501-65-5

Diphenylacetylene

Phenyllithium Structure

591-51-5

Phenyllithium

N/A Structure

189343-66-6

N/A

~78%

Diphenylacetylene Structure

501-65-5

Diphenylacetylene

1-(Phenoxymethyl)-1H-benzotriazole Structure

111198-02-8

1-(Phenoxymethy...

~%

Diphenylacetylene Structure

501-65-5

Diphenylacetylene

2-(1H-1,2,3-benzotriazol-1-yl)-1,2-diphenylethanone Structure

147861-19-6

2-(1H-1,2,3-ben...

~%

Diphenylacetylene Structure

501-65-5

Diphenylacetylene

2-(1H-benzo[d][1,2,3]triazol-1-yl)-2-phenoxy-1-phenylethan-1-one Structure

189343-53-1

2-(1H-benzo[d][...

~%

Diphenylacetylene Structure

501-65-5

Diphenylacetylene


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