A simple and convenient route to 1,2,3,4,5,6,7,8-octahydro-1,6-naphthyridines

Gaidarova, E. L.; Borisenko, A. A.; Chumakov, T. I.; Melnikov, A.; Orlov, Ivan; Grishina, G. V.

doi:10.1016/s0040-4039(98)01662-1

Cited by 8 publications

(4 citation statements)

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“…Piperidine-4-imine derivative Gaidarova et al (1998) demonstrated the synthesis of octahydro-1,6-naphthyridine derivatives (248) by alkylation of piper-idine-4-imine derivative (247) using 1-bromo-3-chloropropane in the presence of a very strong base (LDA or Et 2 NLi) (Scheme 62). [78] The base abstracts a proton from the methylene group of compound 247 (Figure 18). [78] The resultant carbanion intermediate (249) upon alkylation followed by cyclization afforded the endocyclic enamines (248).…”

Section: From Pyrrolo[21-c][14]benzodiazepinementioning

confidence: 99%

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Synthesis of 1,6‐Naphthyridine and Its Derivatives: A Systematic Review

2021

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The naturally and synthetically obtained 1,6-naphthyridine derivatives possess a wide range of pharmacological properties. This factor inspired the medicinal chemists and organic chemists to develop new methods for the synthesis of 1,6-naphthyridine derivatives. This review will discuss the synthesis of 1,6-naphthyridine and its derivatives from diverse starting materials or key intermediates in a systematic manner with appropriate mechanisms.

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Section: From Pyrrolo[21-c][14]benzodiazepinementioning

confidence: 99%

“…[78] The base abstracts a proton from the methylene group of compound 247 (Figure 18). [78] The resultant carbanion intermediate (249) upon alkylation followed by cyclization afforded the endocyclic enamines (248).…”

Section: From Pyrrolo[21-c][14]benzodiazepinementioning

confidence: 99%

Synthesis of 1,6‐Naphthyridine and Its Derivatives: A Systematic Review

2021

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“…We planned to obtain seven-membered enamines XVI-XVIII according to the procedure developed by us previously for the preparation of their six-membered analogs, 1,2,3,4,5,6,7,8-octahydro-1,6-naphthyridines [1].…”

Section: Short Communicationsmentioning

confidence: 99%

2,3,4,5,6,7,8,9-Octahydro-1H-pyrido[4,3-b]azepines. Synthesis and Properties

2005

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SHORT COMMUNICATIONSThe synthesis and chemical properties of 1,7-disubstituted 2, 3,4,5,6,7,8,9-octahydro-1H-pyrido[4,3-b]azepines were studied. These compounds belong to a new heterocyclic system containing an endocyclic enamine fragment. Compounds XIII-XV were synthesized via a series of consecutive reactions including lithiation of 4-iminopiperidines I-III with lithium diethylamide, alkylation of lithium salts IV-VI with 1-bromo-4-chlorobutane, nucleophilic substitution of the chlorine atom in 3-(4-chlorobutyl)imines VII-IX by iodine, and intramolecular cyclization of 3-(4-iodobutyl)imines X-XII to target 1,7-disubstituted pyrido-[4,3-b]azepinium salts XIII-XV by heating in boiling acetonitrile. All these reactions were carried out without isolation of intermediate products VII-XV.We planned to obtain seven-membered enamines XVI-XVIII according to the procedure developed by us previously for the preparation of their six-membered analogs, 1,2,3,4,5,6,7,8-octahydro-1,6-naphthyridines [1].However, no cyclization of intermediate VII (R = Ph) to desired azepine XVI occurred under the conditions optimal for the synthesis of 1,6-naphthyridines. We succeeded in obtaining azepinium salt XIII only via cyclization of the corresponding iodide X which was prepared by nucleophilic substitution of the chlorine atom in 1-benzyl-3-(4-chlorobutyl)-4-phenyliminopiperidine (VII) by iodine on heating with NaI in boiling acetonitrile. 6-Benzyl-1-phenyl-2, 3,4,5,6,7,8,9octahydro-1H-pyrido[4,3-b]azepine (XVI) was isolated by treatment of salt XIII with alkali. The structure of enamine XVI was determined on the basis of the GC-MS data, MALDI spectra (using positive and negative ion registration), and 1 H and 13 C NMR

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“…The procedure involves metallation of imines 152 with lithium diisopropylamide or diethylamide followed by alkylation of the lithium derivatives with 1,3-bromochloropropane and intramolecular cyclisation of the resulting chloroalkylamines. 110 2-Benzyl-1,6-dimethyl-3,10-di(methoxycarbonyl)-8-phenyldecahydro-1,6-naphthyridin-4-one was synthesised and its structure was confirmed by X-ray diffraction analysis. 111 At the end of the section dealing with the synthesis of 1,6naphthyridines, let us consider special procedures for the preparation of their annelated analogues.…”

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confidence: 99%