The attempted Baylis-Hillman reactions of sulfonyl aldimines or aryl aldehydes with 3-methylpenta-3,4-dien-2-one or 3-benzylpenta-3,4-dien-2-one gave the corresponding Baylis-Hillman adducts in moderate yields in DMSO...The attempted Baylis-Hillman reactions of sulfonyl aldimines or aryl aldehydes with 3-methylpenta-3,4-dien-2-one or 3-benzylpenta-3,4-dien-2-one gave the corresponding Baylis-Hillman adducts in moderate yields in DMSO under the catalysis of DBU or PMe3, respectively. Moderate diastereoselectivities were observed in the reaction of 3-benzylpenta-3,4-dien-2-one with N-arylmethylidene-1-naphthalenesulfonamides catalyzed by chiral catalyst cinchona alkaloid derivative TQO {4-（3-ethyl-4-oxa-1-azatricyclo[4.4.0.0^3,8]dec-5-yl）quinolin-6-ol}.展开更多
A novel one-pot protocol for the synthesis of valuable 3,4-dihydropyridin-2-ones from the condensation of al- dehyde with cyanoacetamide and 1,3-dicarbonyl compounds in the presence of imidazole was developed. A serie...A novel one-pot protocol for the synthesis of valuable 3,4-dihydropyridin-2-ones from the condensation of al- dehyde with cyanoacetamide and 1,3-dicarbonyl compounds in the presence of imidazole was developed. A series of aldehydes and 1,3-dicarbonyl compounds were employed to examine the scope of substrates for this protocol. This reaction proceeded through the formation of one ring and four new bonds （two C-C, one C-N, one C=C） via the sequence involving Knoevenagel condensation, Michael addition and intramolecular cyclization with moderate to excellent yields. All new compounds were characterized by IR, 1H NMR, 13C NMR and HRMS.展开更多
l-Benzoxepino(3, 4-b)quinolin-l3(6H)-one and its halogen,alkyl, alkoxy derivatives Va'-d' and 1-benzothiepino(3,4-b}-quinolin- 13 ( 6H)-one Vf, and its alkyl derivatives Vg, weresynthesized through cyclization...l-Benzoxepino(3, 4-b)quinolin-l3(6H)-one and its halogen,alkyl, alkoxy derivatives Va'-d' and 1-benzothiepino(3,4-b}-quinolin- 13 ( 6H)-one Vf, and its alkyl derivatives Vg, weresynthesized through cyclization of 2-(substituted phenoxymethyl)-3-quinolinecarboxylic acids Va-d and 2-[ (un)substituted phen-ylthiomethyll-3-quinolinecarboxylic acids IVf-g in the presence ofpolyphosphoric acid.The acids IV were obtained from the corresponding ethyl-esters @ whcih were prepared through refluxing ethyl 2-bromo-methyl-3-quinolinecarboxylate(1) with substituted phenol or (un)substituted thiophenol in the presence of NaOEt.The compound Vg, was allowed to react with NBS, KaBH4, NH2OH-HCl to give compounds VII , VIII, and IX, respectively.The structures of 24 new compounds have been confirmed by elemental analysis, IR and 1H NMR.展开更多
基金Project supported by State Key Project of Basic Research （Project 973） （No. G2000048007）, Shanghai Municipal Committee of Science and Technology （Nos. 04JC14083, 06XD14005）, and the National Natural Science Foundation of China （Nos. 20472096, 203900502, and 20672127）.
文摘The attempted Baylis-Hillman reactions of sulfonyl aldimines or aryl aldehydes with 3-methylpenta-3,4-dien-2-one or 3-benzylpenta-3,4-dien-2-one gave the corresponding Baylis-Hillman adducts in moderate yields in DMSO under the catalysis of DBU or PMe3, respectively. Moderate diastereoselectivities were observed in the reaction of 3-benzylpenta-3,4-dien-2-one with N-arylmethylidene-1-naphthalenesulfonamides catalyzed by chiral catalyst cinchona alkaloid derivative TQO {4-（3-ethyl-4-oxa-1-azatricyclo[4.4.0.0^3,8]dec-5-yl）quinolin-6-ol}.
基金The financial support from the National Natural Science Foundation of China （No. 21072172） and the Zhejiang Provincial Natural Science Foundation （No. 2010-Z4090225） is gratefully acknowledged.
文摘A novel one-pot protocol for the synthesis of valuable 3,4-dihydropyridin-2-ones from the condensation of al- dehyde with cyanoacetamide and 1,3-dicarbonyl compounds in the presence of imidazole was developed. A series of aldehydes and 1,3-dicarbonyl compounds were employed to examine the scope of substrates for this protocol. This reaction proceeded through the formation of one ring and four new bonds （two C-C, one C-N, one C=C） via the sequence involving Knoevenagel condensation, Michael addition and intramolecular cyclization with moderate to excellent yields. All new compounds were characterized by IR, 1H NMR, 13C NMR and HRMS.
文摘l-Benzoxepino(3, 4-b)quinolin-l3(6H)-one and its halogen,alkyl, alkoxy derivatives Va'-d' and 1-benzothiepino(3,4-b}-quinolin- 13 ( 6H)-one Vf, and its alkyl derivatives Vg, weresynthesized through cyclization of 2-(substituted phenoxymethyl)-3-quinolinecarboxylic acids Va-d and 2-[ (un)substituted phen-ylthiomethyll-3-quinolinecarboxylic acids IVf-g in the presence ofpolyphosphoric acid.The acids IV were obtained from the corresponding ethyl-esters @ whcih were prepared through refluxing ethyl 2-bromo-methyl-3-quinolinecarboxylate(1) with substituted phenol or (un)substituted thiophenol in the presence of NaOEt.The compound Vg, was allowed to react with NBS, KaBH4, NH2OH-HCl to give compounds VII , VIII, and IX, respectively.The structures of 24 new compounds have been confirmed by elemental analysis, IR and 1H NMR.
