e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

Synthesis of 2-alkoxy (aroxy)-3-substituted quinolines by DABCO-promoted cyclization of o-alkynylaryl isocyanides

J Zhao, C Peng, L Liu, Y Wang…

Index: Zhang, Qi; Wang, Deping; Wang, Xianyang; Ding, Ke Journal of Organic Chemistry, 2009 , vol. 74, # 18 p. 7187 - 7190

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Citation Number: 25

Abstract

Diversified 2-alkoxy-and 2-aroxy-3-substituted quinolines were synthesized from o- alkynylaryl isocyanides and alcohols and phenols promoted by DABCO, respectively. The reaction was initiated by nucleophilic addition of DABCO to isocyanide and subsequent

3,5-Dimethoxyphenol Structure

3,5-Dimethoxyphenol

4-Bromotoluene Structure

~90%

1,3-dimethoxy-5-(4-methylphenoxy)benzene Structure

1,3-dimethoxy-5...

o-cresol Structure

Chlorobenzene Structure

~44%

Benzene,1-methyl-2-phenoxy- Structure

Benzene,1-methy...

1-Iodo-3,5-dimethylbenzene Structure

1-Iodo-3,5-dime...

Phenol Structure

~96%

3,5-Dimethylphenylphenyl ether Structure

3,5-Dimethylphe...

Bromobenzene Structure

4-Hydroxybenzonitrile Structure

4-Hydroxybenzon...

~63%

4-Phenoxybenzonitrile Structure

4-Phenoxybenzon...

3-Chloropyridine Structure

3-Chloropyridine

Mequinol Structure

~79%

3-(4-methoxyphenoxy)pyridine Structure

3-(4-methoxyphe...

4-Bromoacetanilide Structure

4-Bromoacetanilide

Phenol Structure

~94%

Acetamide,N-(4-phenoxyphenyl)- Structure

Acetamide,N-(4-...

Bromobenzene Structure

4-Acetamidophenol Structure

4-Acetamidophenol

~93%

Acetamide,N-(4-phenoxyphenyl)- Structure

Acetamide,N-(4-...

3-Bromopyridine Structure

3-Bromopyridine

o-cresol Structure

~89%

3-(O-TOLYLOXY)PYRIDINE Structure

3-(O-TOLYLOXY)P...

3-Iodopyridine Structure

o-cresol Structure

~96%

3-(O-TOLYLOXY)PYRIDINE Structure

3-(O-TOLYLOXY)P...

4-Bromobenzyl alcohol Structure

4-Bromobenzyl a...

Phenol Structure

~82%

(4-Phenoxyphenyl)Methanol Structure

(4-Phenoxypheny...

4-Bromoaniline Structure

Phenol Structure

~68%

4-Phenoxyaniline Structure

4-Phenoxyaniline

Bromobenzene Structure

Methyl 4-hydroxybenzoate Structure

Methyl 4-hydrox...

~71%

4-Phenoxybenzoic acid methyl ester Structure

4-Phenoxybenzoi...