γ-Pyridones by Isomerization. Substituted 1-Methyl-3,5-dibenzyl-4-pyridones

Leonard, Nelson J.; Locke, David M.

doi:10.1021/ja01612a042

Cited by 31 publications

(6 citation statements)

References 0 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…496-498 K (literature m.p. 496-498 K; Leonard & Locke, 1955). Good quality crystal used for data collection from: (III) mixture of 2-propanol and 95% EtOH, (IV) mixture of MeOH and hexane.…”

Section: Methodsmentioning

confidence: 99%

Structures of 2,6-bis(benzylidene)cyclohexanone (III) and 3,5-bis(4-dimethylaminobenzylidene)-1-methyl-4-piperidone (IV)

Zeng¹,

Quail²,

Arora³

et al. 1989

Acta Crystallogr C

View full text Add to dashboard Cite

Section: Methodsmentioning

confidence: 99%

Structures of 2,6-bis(benzylidene)cyclohexanone (III) and 3,5-bis(4-dimethylaminobenzylidene)-1-methyl-4-piperidone (IV)

Zeng¹,

Quail²,

Arora³

et al. 1989

Acta Crystallogr C

View full text Add to dashboard Cite

“…The structures of the known 3,5-bis[(hetero)arylidene]piperidin-4-ones 2a [18], 2c [19], 2e [20], 2f [21], and 3a [22] obtained via Methods A and B as free bases were confirmed by the multinuclear NMR spectra. Their physicochemical constants fit well the available literature data.…”

mentioning

confidence: 81%

“…As Lewis bases, Bu 3 P and Ph 3 P, useful as catalysts for the Morita -Baylis -Hillman reaction [11], intramolecular aldol condensations [12], and others, were also used. As a model, the reaction of N-methylpiperidin-4-one (1a) with 4-fluorobenzaldehyde was chosen as it allowed easy monitoring of the reaction course by 19 F-NMR spectroscopy. In Table 1, the results obtained for this reaction are collected.…”

mentioning

confidence: 99%

“…19 (6)); 111.14 (C(11), C(11')); 118.24 (CN); 130.70 (C(9), C(9'), C(13), C(13')); 132.18 (C(10), C(10'), C(12), C(12')); 132.77 (C(7), C(7')); 135.98 (C(3), C (5) 1604m, 1586m, 1415w, 1290w, 1272s, 1198w, 1173w, 1083s, 1074s, 1026s, 941w, (6)); 112.23 (C(11), C(11')); 118.48 (CN); 129.52 (C(9), C(9'), C(13), C(13')); 131.28 (C(10), C(10'), C(12), C(12')); 132.70 (C(7), C(7')); 138.12 (C(3), C(5)); 137.98 (C(8), C(8')); 181.38 (C(4)). 1602w, 1552m, 1467m, 1270m, 1211m, 1175s, 1084s, 1060s, 1034s, 980m, 939w, 804w, 767w, 678m, 534m, 522m.…”

mentioning

confidence: 99%

“…19 1500w, 1410m, 1314w, 1290s, 1182s, 1168m, 1082s, 964m, 918m, 852m, (6)); 112.31 (C(11), C(11')); 118.71 (CN); 130.37 (C(9), C(9'), C(13), C(13')); 131.30 (C(10), C(10'), C(12), C(12')); 132.89 (C(7), C(7')); 137.89 (C(3), C (5) NH-Piperidin-4-one (1 mmol) and 4-formylbenzonitrile (2 mmol) were dissolved in glacial AcOH (3 ml) · HCl (prepared from NH 4 Cl, 5 mmol) was bubbled through the soln. The soln.…”

mentioning

confidence: 99%

See 2 more Smart Citations

Lewis Acids as Mild and Effective Catalysts for the Synthesis of 3,5‐Bis[(hetero)arylidene]piperidin‐4‐ones

Leonova

Makarov

Klemenkova

et al. 2010

Helvetica Chimica Acta

View full text Add to dashboard Cite

The aldol-crotonic condensation reactions of N-alkyl-and NH-piperidin-4-one derivatives with (hetero)aromatic aldehydes promoted by Lewis acids or bases were examined. This comparative study has revealed three effective catalytic systems based on Lewis acids, i.e., LiClO 4 and MgBr 2 (in the presence of tertiary amine), and BF 3 · Et 2 O, for the synthesis of N-alkyl-substituted 3,5-bis(heteroarylidene)piperidin-4-ones, including those bearing acid-or base-labile groups both in the (hetero)aromatic groups and in the alkyl substituent at the N-atom. The highest reaction rate was observed for LiClO 4 -mediated synthesis. Both MgBr 2 -and LiClO 4 -mediated syntheses were inefficient in the case of NH-piperidin-4-one, while BF 3 · Et 2 O provided the final compounds in high yields. This catalyst is especially advantageous as it allows simultaneous condensation and deprotection in the case of Oprotected piperidin-4-one.

show abstract

The Aldol Condensation

Nielsen

Houlihan²

2011

Organic Reactions

View full text Add to dashboard Cite

The aldol condensation takes its name from aldol (3‐hydroxybutanal) a name introduced by Wurtz who first prepared the beta‐hydroxy aldehyde from acetaldehdye in 1872. The aldol condensation includes reactions producing beta‐hydroxy aldehydes or beta‐hydroxy ketones by self condensations or mixed condensations of aldehydes and ketones as well as reactions leading to alpha, beta‐unsaturated aldehydes or alpha,beta‐unsaturated ketones formed by dehydration of intermediate beta‐aldols or beta‐ketals. The Claisen‐Schmidt condensation is most often taken to be the condensation of an aromatic aldehyde or ketone usually in the presence of a basic catalyst. The term aldol condensation has also been applied to many other condensations involving the reaction of an aldehyde or ketone. These condenations are discussed. The present review includes examples that are solely condensation reactions of aldehydes and ketones.

show abstract

γ-Pyridones by Isomerization. Substituted 1-Methyl-3,5-dibenzyl-4-pyridones

Cited by 31 publications

References 0 publications

Structures of 2,6-bis(benzylidene)cyclohexanone (III) and 3,5-bis(4-dimethylaminobenzylidene)-1-methyl-4-piperidone (IV)

Structures of 2,6-bis(benzylidene)cyclohexanone (III) and 3,5-bis(4-dimethylaminobenzylidene)-1-methyl-4-piperidone (IV)

Lewis Acids as Mild and Effective Catalysts for the Synthesis of 3,5‐Bis[(hetero)arylidene]piperidin‐4‐ones

The Aldol Condensation

Contact Info

Product

Resources

About