Eine neue Synthese des Bz‐Tetrahydrochinolins

3-Formylchromone(1) reacts with active methylene derivatives to yield condensation products 2a-d, 1 0 , l l and 12. Treatment of 2a-d with ammonia or methylamine gives pyridines 3-6. Alternatively, reaction of 1 with enamine derivatives yields pyrido compounds 15, 17, 19, 21, 23 and 28 in one step. Factors determining the formation and regiospecificity of the pyridine ring forming reactions are also discussed.1.

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“…Found: C,58.94;H,2.84;N,9.79. (3,3,6,6-Tetramethyl-l,8-dioxo-l,2,3,4,5,6,7,8-octahydroxanthen-9-yl)chromone (12).…”

Section: -(4-0~0-4h-benzopyran-3-yimethylene)barbituricmentioning

confidence: 99%

“…0~0-1,2,3,4-tetrahydro-6-hydroxy[ l]benzopyrano[4.3-b]quinoline (21). (1) (1 7.4 g. 100 mmoles), 3-amino-2-cyclohexen-lone (20) (12) (11.1 g., 100 mmoles) and 166 ml. of pyridine were heated under reflux for 5 hours.…”

Section: -mentioning

confidence: 99%

The synthesis of pyridine derivatives from 3‐formylchromone

Haas

Stanton

Sprecher

et al. 1981

Journal of Heterocyclic Chem

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“…The open ring compounds 5 and 6 ( Table 1) were obtained by reaction of the ketones 5b and 6b with NaBH 4 and subsequent conversion with CDI (Scheme 4). For the synthesis of compound 6b, the pyridine N-oxide 6a was prepared from 3-acetylpyridine and ethylene glycol [11] and subsequent Noxidation of the ketal using benzonitrile/H 2 O 2 (pH: [8][9] according to the method of Payne et al [12] . O-Methylation of the N-oxide using dimethyl sulfate and subsequent reaction of the crude product with KCN under alkaline conditions and exclusion of oxygen afforded the nitrile 6c.…”

Section: Methodsmentioning

confidence: 99%

“…For the synthesis of compound 1 the ketone 1b [8] had to be prepared first (Scheme 1). Compound 1b was obtained by reaction of propinal with 3-aminocyclohex-2-en-1-one in DMF.…”

Section: Chemistrymentioning

confidence: 99%

1-Imidazolylcarbonyloxy-substituted Tetrahydroquinolines and Pyridines: Synthesis and Evaluation of P450 TxA2 Inhibition

Hartmann

Frotscher

1999

Arch. Pharm. Pharm. Med. Chem.

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The title compounds are derived from our model describing structural requirements for strong P450 TxA2 inhibition [1]. In the present paper the syntheses of the 1‐imidazolylcarbonyloxy‐substituted tetrahydroquinolines 1, 3, and 4, tetrahydro‐naphthalene 2 and 3‐ethylpyridines 5 and 6 are described. Using our P450 TxA2 inhibition assay, 1—6 were tested for enzyme inhibitory activity. Compound 1 (5‐(1‐imidazolylcarbonyloxy)‐5,6,7,8‐tetrahydroquinoline) turned out to be the most active derivative showing a potency similar to the reference compound dazoxiben (IC50 values 1.6 and 1.1 μM).

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“…The importance of nucleophilicity of the nitrogen to form enamines has been documented and it can be determined by stereoeletronic effects of amines. [41][42][43][44] As shown in Table 1, the reactions where more nucleophilic amines were used (i.e. benzylamine, cyclohexylamine, and hexylamine) gave the products in almost quantitative yields in a short period of time.…”

mentioning

confidence: 99%