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<p>Systematic study on acylation of methyl 3-aminocrotonate with acid chlorides of aliphatic, aromatic and α, β-unsaturated acids: A comparative evaluation of the preference for regio- and stereoselectivity <em>vis</em><em>-</em><em>à</em><em>-</em><em>vi</em>s 3-aminocrotononitrile</p><p> </p><p><strong> </strong></p><strong><p> </p></strong>

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Title Statement <p>Systematic study on acylation of methyl 3-aminocrotonate with acid chlorides of aliphatic, aromatic and α, β-unsaturated acids: A comparative evaluation of the preference for regio- and stereoselectivity <em>vis</em><em>-</em><em>à</em><em>-</em><em>vi</em>s 3-aminocrotononitrile</p><p> </p><p><strong> </strong></p><strong><p> </p></strong>
 
Added Entry - Uncontrolled Name Mukherjee, Attreyee ; Ananda Mohan College, Kolkata 700 009, India
Mahalanabis, Kumar K; Jadavpur University, Kolkata 700 032, India
Jadavpur University, Kolkata
 
Uncontrolled Index Term Methyl 3-aminocrotonate, acylation, enaminones, enamides, regioselective, stereoselective
 
Summary, etc. <p>Acylation of methyl 3-aminocrotonate <strong>1a</strong> in benzene with a variety of aliphatic and aromatic acid chlorides including α, β-unsaturated acid chloride in the presence of an added organic base, (either pyridine or triethylamine) is reported. The preferred N, C-site selectivity in these reactions has been compared with the terminal selectivity of the products obtained previously on acylation of methyl 3-aminocrotononitrile <strong>1b</strong>. A strong preference either for N- or C- selectivity in N, <br /> C-acylation has been observed for both <strong>1a</strong> and <strong>1b</strong> based on the choice of acid chlorides and added organic base. Interestingly, irrespective of the enamine <strong>1a</strong> or <strong>1b</strong>, acylation with α, β-unsaturated acid chlorides in the presence of triethylamine afforded 3,4-dihydropyridin-(2<em>H</em>)-one <em>via</em> [3.3] sigmatropic rearrangement of the corresponding intermediary N(E)-enamide. Accrued results show methyl 3-aminocrotonate to be a better precursor for preparation of enamides <br /> (N-acylated products) whereas 3-aminocrotononitrile is found to be a preferred choice for preparation of enaminones <br /> (C-acylated products). An attempt is made to offer a preliminary theoretical interpretation for observed site selectivity.</p><br />
 
Publication, Distribution, Etc. Indian Journal of Chemistry -Section B (IJC-B)
2021-02-15 15:57:41
 
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http://op.niscair.res.in/index.php/IJCB/article/view/30279
 
Data Source Entry Indian Journal of Chemistry -Section B (IJC-B); ##issue.vol## 60, ##issue.no## 2 (2021): Indian Journal of Chemistry Section - B (IJCB)
 
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