Über Eine Neue Methode zur Darstellung von α‐Pyridonen und Die Synthese des Nicotellins

Thesing, Jan; Müller, A.

doi:10.1002/cber.19570900510

Cited by 48 publications

(10 citation statements)

References 16 publications

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“…ir (potassium bromide): 3195,3093,1668,1628,1572,1522,1401,1346,1166,1009,825,803,790 ,5.23;N,9.09. Found: C,70.26;H,5.14;N,9.01.…”

Section: -(4-bromophenyl)-6-(3-nitrophenyl)-34-dihydropyridin-2 (1hmentioning

confidence: 98%

“…Numerous methods for the preparation of the 4,6-diaryl-2-pyridone template have been reported many times in the literature, such as the synthesis of 3-substituted-2-pyridone [6][7][8] derivatives (A) which are functionalized at the 3 and 4 position. In addition, slight modification of the 4,6-diaryl-2-pyridone nucleus was reported to afford a series of 3-unsubstituted 2-pyridone derivatives [5,[9][10][11] (B) which provide new series of biologically active compounds. Substituted six-membered lactams, 2-pyridones, and their 3,4-dihydro derivatives have also attracted considerable attention from synthetic organic chemists since these scaffolds are found in a wide variety of naturally occurring alkaloids [12] and compounds with these structural motifs have been shown to exhibit significant pharmacological properties [13], for example dihydro-2-pyridones have been applied as scaffolds to the construction of constrained amino acid [14].…”

Section: Introductionmentioning

confidence: 99%

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An efficient microwave‐assisted synthesis of 3,5‐unsubstituted 4‐substituted‐6‐aryl‐3,4‐dihydropyridin‐2(1H)‐ones derivatives

Zhu

Shi

et al. 2007

Journal of Heterocyclic Chem

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Small libraries of 3,5‐unsubstituted 4‐substituted‐6‐aryl‐3,4‐dihydropyridin‐2(1H)‐ones derivatives were synthesized from the condensation‐products of aldehydes with Meldrum's acid, aromatic ketones and ammonium acetate using acetic acid as energy transferring‐agent under microwave irradiation without catalyst. This method has the advantages of excellent yields (65‐90%), short reaction time (5‐10 min) and being environmentally friendly. It aimed to provide new series of potential biologically active compounds for biomedical screening.

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“…ir (potassium bromide): 3195,3093,1668,1628,1572,1522,1401,1346,1166,1009,825,803,790 ,5.23;N,9.09. Found: C,70.26;H,5.14;N,9.01.…”

Section: -(4-bromophenyl)-6-(3-nitrophenyl)-34-dihydropyridin-2 (1hmentioning

confidence: 98%

Section: Introductionmentioning

confidence: 99%

An efficient microwave‐assisted synthesis of 3,5‐unsubstituted 4‐substituted‐6‐aryl‐3,4‐dihydropyridin‐2(1H)‐ones derivatives

Zhu

Shi

et al. 2007

Journal of Heterocyclic Chem

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“…Among the methods for preparation of 3-unsubstituted 2-pyridone, [27][28][29][30][31][32][33][34][35][36][37] [3ϩ3] annulation between chalcone and C-C-N fragment connected with a leaving group displayed high convenience and efficiency, such as N-(2-carbamoylmethyl)-pyridinium ylide, [29][30][31][32][33] 2-acetamidoacetamide 34) or 2-(benzotriazol-1-yl)acetamide. [35][36][37] By scanning the conditions, the best yield (63%) of desired 2-pyridone 8a was obtained when chalcone 7a was refluxed with 2-(benzotriazol-1-yl)acetamide 35) in the presence of NaOH for 6 h. Under similar conditions, other compounds 7b-j were annulated to give the corresponding products 8b-j in 60-75% yields.…”

mentioning

confidence: 99%

Preparation of 2-Pyridone-Containing Tricyclic Alkaloid Derivatives as Potential Inhibitors of Tumor Cell Proliferation by Regioselective Intramolecular N- and C-Acylation of 2-Pyridone

Wang

Cao

Shi

et al. 2005

CHEMICAL & PHARMACEUTICAL BULLETIN

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Recently, A-ring alkoxyl subsitituted b-carbolin-1-ones (1, Chart 1) were reported to inhibit colon and lung tumors in a patent literature.1) Subsequently, we found that 3-aryl b-carbolin-1-ones (2) inhibit the proliferation of HeLa cells with IC 50 values in the low micromolar range and that the aromatic substitution on C3 in 2 proved to be essential for their biological activity.2,3) To broaden the scope of previous studies, aryl-substituted 2-pyridone-containing derivatives, such as pyrido[2,1-a]isoindole-4-one (3) and 1H-indeno[1,2-b]pyridine-2-one (4), were designed as our synthetic targets to make it possible to probe their structure-activity relationships.Some alkaloids having frameworks of 3 and 4 occur in nature, 4-7) whose analogues were synthesized more often in laboratories for their potent bioactivities as receptor ligands, [8][9][10] enzyme inhibitors 11) or anti-tumor agents.12,13)Since 3 and 4 are a pair of structural isomers, it is reasonable to expect that they could be prepared from a common precursor, which should have a structure of 6-substituted 2-pyridone allowing a disconnection between methylene and Cring in 3 and 4 (Chart 1). However, neither such precursor nor procedure has been employed for this purpose so far. [14][15][16][17][18][19][20][21][22][23][24][25][26] Since the methods for preparation of 3-unsubstituted 2-pyridone have been well established in recent years, 27-37) herein we report a novel synthetic route to 3 and 4 as shown in Chart 2. The route starts from an aldol condensation between 2-acetylbenzoic acid (5) and aryl aldehyde (6) to yield chalcone (7), which subsequently undergoes a [3ϩ3] annulation to give 2-(2-pyridon-6-yl)benzoic acid (8). Serving as a common precursor, 8 goes through an intramolecular N-acylation to produce 2-aryl pyrido[2,1-a]isoindole-4,6-diones (9), or carries out an intramolecular C-acylation to yield 4-aryl 1-methyl-1H-indeno[1,2-b]pyridine-2,5-diones (11) regioselectively. Results and DiscussionPreparation of 2-Aryl Pyrido[2,1-a]isoindole-4,6-diones (9a-j) Following the known procedure, 38) the mixtures of 2-acetylbenzoic acid (5) and aryl aldehydes 6a-j were treated respectively with NaOH in aqueous EtOH at room temperature for 20 h. As shown in Table 1, the corresponding products 2-(3-aryl acryloyl)benzoic acids (7a-j) were yielded conveniently in high yields. However, the aryl aldehydes bearing an electron-withdrawing group, such as o-, m-, A novel and practical preparation of 2-pyridone-containing tricyclic alkaloid derivatives was developed. By regioselective intramolecular N-and C-acylation of 2-(4-aryl-2-pyridon-6-yl)benzoic acid, a pair of structural isomers 2-aryl pyrido[2,1-a]isoindole-4,6-diones and 4-aryl 1-methyl-1H-indeno[1,2-b]-pyridine-2,5-diones, as potential inhibitors of tumor cell proliferation, were prepared respectively.

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“…[42][43][44][45][46] Reakcija se najverovatnije odvija prema mehanizmu iniciranom Michaelovom adicijom i ciklizacijom prstena. Retrokondezacija benzilidenaetofenona se odvija do benzaldehida i acetofenona, koji dalje reguje sa benzilidenacetofenonom i amonijum-acetatom gradeći trifenilpiridin prema mehanizmu Chichibabin-ove reakcije, koja uključuje dehidrogenizaciju u poslednjem koraku.…”

Section: Reakcija Kondenzacije Iz αβ-Nezasićenih Karbonilnih Jedinjenjaunclassified

“…47 Alkaloid duvana Nicotellin (2,4-di-(3-piridil)piridin), je sintetisan iz 1-(karbamoilmetil)piridinijum-hlorida i proizvoda Claisen-ove kondezacije između nikotinaldehida i 3-acetilpiridina. 42 Vinilketoni, etil-cijanoacetat i amonijum-acetat daju 3-cijano-4,6-disupstituisane-2-piridone reakcijom koja uključuje Majklovu adiciju i dehidrogenizaciju, pri čemu se intermedijarni 3,4-dihidro-2-piridonski derivat nije detektovan. Ako se koristi benzilidenacetofenon u benzenu, reakcija teče prema mehanizmu koji uključuje Knoevenagel-ovu kondezaciju, i tada je moguće izolovati 3-cijano-5,6-dihidro-4,6-difenil-2-piridon, koji se može da dehidrogenizuje u ključalom acetonu do 2-piridona (Slika 1.18, a)).…”

Section: Reakcija Kondenzacije Iz αβ-Nezasićenih Karbonilnih Jedinjenjaunclassified

Study of the synthesis, structure and properties of the derivatives of 4,6-disubstituted-3-cyano-2-pyridones

Marinković¹

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DSP jednačina koja uključuje nelinearnu karakteristiku rezonancionog efekta supstituenta naziva se DSP-NLR (dvoparametarska jednačina sa nelinearnom karakteristikom rezonancionog efekta) jednačina:Određivanjem veličine parametra ε, definisane su veličine zahteva pojedinih ugljenikovih atoma za elektronima. Poređenjem rezultata korelacija ispitivanih jedinjenja sa literaturnim podacima za jedinjenja koja imaju bočni niz, uspešno i detaljno su razdvojeni i objašnjeni doprinosi različitih efekata supstituenata na polarni (induktivni, efekat polja i π-polarizacija) i rezonancioni, a nagovešten je i uticaj sternog efekta orto-supstituenata.Reversna polarizacija je uočena za određen broj ugljenikovih atoma u slučaju negativnih vrednosti konstanti proprocionalnosti dobijenih primenom LFER jednačina.Rezultati korelacija ukazuju da se prenos elektronskih efekata supstituenta prevashodno odigrava polarizacijom π-lokalizovanih jedinica piridonskog jezgra, pri čemu doprinosi lokalizovane i proširene π-polarizacije zavise od prisutnog supstituenta.U cilju definisanja potpune geometrije ispitivanih jedinjenja izračunate su konformacije sa minimumom energije primenom semi-empirijske MO PM6 metode, kao i B3LYP (DFT) hibridne metode. Neplanarnost N-i supstituisanog fenilnog jezgra u polžaju 4 piridonskog prstena je određena veličinom torzionih uglova između 4-i 6-fenilnih jezgara i piridonskog prstena u seriji 3-cijano-4-(supstituisani fenil)-6-fenil-2(1H)-piridona, kao i N-fenilnog jezgra i piridonskog prstena u seriji N-(supstituisani fenil)-3-cijano-4,6-dimetil-2-piridona. Načini prenosa efekata supstituenata su razmatrani u svetlu izračunatih geometrija sa minimalnom energijom.Imajući u vidu rezultate istraživanja i odgovarajuća tumačenja iznesena u ovoj disertaciji, može se zaključiti da su mehanizmi prenosa elektronskih efekat supstituenata kompleksni. Na osnovu rezultata korelacija dobijenih LFER analizom može se konstantovati da se sve, a posebno DSP-NLR jednačina kojom se adekvatno objašnjava nelinearni doprinos rezonancionog efekta ukupnom efektu supstituenta, mogu koristiti za objašnjenje prenosa efekata kroz ispitivane sisteme.Analiza MS i MS/MS spektara 3-cijano-4-(supstituisani fenil)-6-fenil-2(1H)-piridona, dobijenih elektron jonizacijom, ukazuje na veličinu doprinosa elektronskih efekata supstituenata i njihove geometrije na fragmentacione puteve i intenzitete uočenih jona.Takođe, primenom elektro-sprej masene spektrometrije uočen je i diskutovan uticaj elektronskih efekata prisutnih supstituenata i geometrije 3-cijano-4-(supstituisani fenil)-6-fenil-2(1H)-piridona na njihove fragmentacione puteve, kao i uticaj tautomernih oblika ispitivanih jedinjenja (2-piridon/2-hidroksipiridin). Ispitivana jedinjenja u primenjenim uslovima ESI jonizacije grade dvostruko naelektrisane klastere koji imaju značajan intenzitet u MS spektrima. Jedinjenja koja imaju jake elektron-donorske grupe pokazuju značajan afinitet prema protonu, a time usled protonovanja fragmentacije supstituenta su najintenzivniji procesi u odgovarajućim s...

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Über Eine Neue Methode zur Darstellung von α‐Pyridonen und Die Synthese des Nicotellins

Cited by 48 publications

References 16 publications

An efficient microwave‐assisted synthesis of 3,5‐unsubstituted 4‐substituted‐6‐aryl‐3,4‐dihydropyridin‐2(1H)‐ones derivatives

An efficient microwave‐assisted synthesis of 3,5‐unsubstituted 4‐substituted‐6‐aryl‐3,4‐dihydropyridin‐2(1H)‐ones derivatives

Preparation of 2-Pyridone-Containing Tricyclic Alkaloid Derivatives as Potential Inhibitors of Tumor Cell Proliferation by Regioselective Intramolecular N- and C-Acylation of 2-Pyridone

Study of the synthesis, structure and properties of the derivatives of 4,6-disubstituted-3-cyano-2-pyridones

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