Synthesis of substituted tetrahydropyridines and M-hydroxybenzoic acids

Clinch, Keith; Márquez, César; Parrott, Maxwell J.; Ramage, R.

doi:10.1016/0040-4020(89)80052-3

Cited by 24 publications

(5 citation statements)

References 19 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…An interesting new strategy for preparing a variety of substituted thp compounds (e.g., 5-and 6-methylarecoline) has been published. 24 This method, which in concept also provides novel prodrugs of areca and ergot alkaloids, relies on a 1,6-intramolecular Michael addition of methoxycarbonyl-2,4-dienylamines.…”

Section: Resultsmentioning

confidence: 99%

Cholinergic Agents: Effect of Methyl Substitution in a Series of Arecoline Derivatives on Binding to Muscarinic Acetylcholine Receptors

Moos¹,

Bergmeier²,

Coughenour³

et al. 1992

Journal of Pharmaceutical Sciences

View full text Add to dashboard Cite

Section: Resultsmentioning

confidence: 99%

Cholinergic Agents: Effect of Methyl Substitution in a Series of Arecoline Derivatives on Binding to Muscarinic Acetylcholine Receptors

Moos¹,

Bergmeier²,

Coughenour³

et al. 1992

Journal of Pharmaceutical Sciences

View full text Add to dashboard Cite

“…91 (d) Stobbe condensation of a succinic ester [92][93][94][95] or (e) Wittig olefination of a succinic ester-derived phosphorane 96,97 with an aldehyde, followed by Curtius reaction and hydrogenation. (f) Hydrolysis of either 5-substituted dihydrouracils 98 -100 or 4-substituted pyrazolines.…”

Section: Enantioselective Synthesis Of ␤ 2 -Amino Acids Via Chiral ␤-mentioning

confidence: 99%

β²‐amino acids—syntheses, occurrence in natural products, and components of β‐peptides^1,2

2004

View full text Add to dashboard Cite

Although they are less abundant than their alpha-analogues, beta-amino acids occur in nature both in free form and bound to peptides. Oligomers composed exclusively of beta-amino acids (so-called beta-peptides) might be the most thoroughly investigated peptidomimetics. Beside the facts that they are stable to metabolism, exhibit slow microbial degradation, and are inherently stable to proteases and peptidases, they fold into well-ordered secondary structures consisting of helices, turns, and sheets. In this respect, the most intriguing effects have been observed when beta2-amino acids are present in the beta-peptide backbone. This review gives an overview of the occurrence and importance of beta2-amino acids in nature, placing emphasis on the metabolic pathways of beta-aminoisobutyric acid (beta-Aib) and the appearance of beta2-amino acids as secondary metabolites or as components of more complex natural products, such as peptides, depsipeptides, lactones, and alkaloids. In addition, a compilation of the syntheses of both achiral and chiral beta2-amino acids is presented. While there are numerous routes to achiral beta2-amino acids, their EPC synthesis is currently the subject of many investigations. These include the diastereoselective alkylation and Mannich-type reactions of cyclic- or acyclic beta-homoglycine derivatives containing chiral auxiliaries, the Curtius degradation, the employment of transition-metal catalyzed reactions such as enantioselective hydrogenations, reductions, C-H insertions, and Michael-type additions, and the resolution of rac. beta2-amino acids, as well as several miscellaneous methods. In the last part of the review, the importance of beta2-amino acids in the formation of beta-peptide secondary structures is discussed.

show abstract

“…In this case, the overall ring closure process is very fast and compound 3 could be isolated only in the presence of less than one equivalent of base. The benzannulation procedure is usually performed at low temperature (from −30 to 20 °C) with diphenylphosphinic chloride,14 ethyl chloroformate15 or trifluoroacetic anhydride16 as activating agents and a tertiary amine (triethyl amine, N ‐methylmorpholine) as base. Otherwise, stronger conditions are necessary to induce the cyclization of ynenylketene 6 .…”

Section: General Features In Benzannulation and Preparation Of 3‐alkomentioning

confidence: 99%

“…The first preparation of substituted m ‐hydroxybenzoic acids by benzannulation of 3‐methoxycarbonyl‐3,5‐hexadienoic acids ( 1 ; R 3 =H, R 4 =Me) was by Ramage et al 14. These authors prepared the above‐mentioned acids by Wittig reaction of ylide 11 b with α,β‐unsaturated aldehydes, followed by regioselective acid hydrolysis of the tert ‐butyl ester.…”

Section: Preparation Of Biaryls Terphenyls Triphenylenes and Heteromentioning

confidence: 99%

Recent Advances in the Benzannulation of Substituted 3‐Alkoxycarbonyl‐3,5‐hexadienoic Acids and 3‐Alkoxycarbonylhex‐3‐en‐5‐ynoic Acids to Polysubstituted Aromatics

Serra

Fuganti

Brenna

2007

Chemistry A European J

View full text Add to dashboard Cite

The benzannulation reactions of substituted 3-alkoxycarbonyl-3,5-hexadienoic and 3-alkoxycarbonylhex-3-en-5-ynoic acids offer a straightforward access to various polysubstituted aromatic compounds. The process is very flexible, and can be applied to the regiospecific preparation of oligoaryls, naphthalenes, ring-fused heterocycles, chiral tetrahydronaphthalenes, C-aryl-glycosides and many natural products of different structure. In this Concept article, we highlight the potential of this annulation reaction by illustration of our recent contribution to this field, as well as the studies previous reported by others.

show abstract

Synthesis of substituted tetrahydropyridines and M-hydroxybenzoic acids

Cited by 24 publications

References 19 publications

Cholinergic Agents: Effect of Methyl Substitution in a Series of Arecoline Derivatives on Binding to Muscarinic Acetylcholine Receptors

Cholinergic Agents: Effect of Methyl Substitution in a Series of Arecoline Derivatives on Binding to Muscarinic Acetylcholine Receptors

β²‐amino acids—syntheses, occurrence in natural products, and components of β‐peptides^1,2

Recent Advances in the Benzannulation of Substituted 3‐Alkoxycarbonyl‐3,5‐hexadienoic Acids and 3‐Alkoxycarbonylhex‐3‐en‐5‐ynoic Acids to Polysubstituted Aromatics

Contact Info

Product

Resources

About

Synthesis of substituted tetrahydropyridines and M-hydroxybenzoic acids

Cited by 24 publications

References 19 publications

Cholinergic Agents: Effect of Methyl Substitution in a Series of Arecoline Derivatives on Binding to Muscarinic Acetylcholine Receptors

Cholinergic Agents: Effect of Methyl Substitution in a Series of Arecoline Derivatives on Binding to Muscarinic Acetylcholine Receptors

β2‐amino acids—syntheses, occurrence in natural products, and components of β‐peptides1,2

Recent Advances in the Benzannulation of Substituted 3‐Alkoxycarbonyl‐3,5‐hexadienoic Acids and 3‐Alkoxycarbonylhex‐3‐en‐5‐ynoic Acids to Polysubstituted Aromatics

Contact Info

Product

Resources

About

β²‐amino acids—syntheses, occurrence in natural products, and components of β‐peptides^1,2