Synthesis of 7a,8,9,10-tetrahydro-2,3,5,6,7a-pentaazapyrene

Smetskaya, N. I.; Zhidkova, A. M.; Mukhina, N. A.; Граник, В. Г.

doi:10.1007/bf00506416

Cited by 3 publications

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“…Die Kondensation der Aminale 3 mit CH2-aciden Verbindungen konnte auch zu Produkten 18 fuhren, die konstitutionsisomer zu den Butadienen 10 sind, nam- lich dann, wenn sich das Anion der CH2-aciden rerbindung nicht wie vorgeschlagen an das C1, sondern an das C3 des ambidenten Kations 12 addiert und aus dem so gebildeten Allen 17 durch Prototropie das Butadien 18 entsteht. [28] und 2-Cyan-3-methyl-but-2-ensaure-Derivaten [29] sind ebenfalls beschrieben.…”

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Orthoamide. L. Beiträge zur Chemie von Propiolaldehydaminalen - Synthesen und Umsetzungen zu Push-Pull-substituierten Buta-1,3-dienen, Cyclobutanen sowie vinylogen Amidiniumsalzen und 1,2,3-Triazolen

1997

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Orthoamides. L. Contribution to the Chemistry of Propiolaldehydaminales – Synthesis and Transformations to Push–Pull‐substituted Buta‐1,3‐dienes, Cyclobutanes, Vinylogous Amidinium Salts and 1,2,3‐Triazoles Tert‐butylaminalester 5 reacts with terminal alkynes to give aminals of substituted propiolaldehydes 3c, d. The aminal 3a is accessible from N,N,N′,N′‐tetramethylformamidinium chloride (7b) and sodium acetylide. The aminals 3b,c can also be prepared from bis(dimethylamino)acetonitrile 8 and terminal alkynes in the presence of sodium hydride. The nitrile 8 is also useful for the preparation of the bis‐aminal of acetylenedialdehyde 6. The aminal 3e can be transaminated by heating with secondary amines to give the aminals 3f–i. The aminals 3a–i react with strong CH2‐acidic compounds (pKa between 9 and 14) to give the 1‐dialkylamino‐1,3‐butadienes 10. The isomeric 1‐dialkylamino‐butadienes 18 can be obtained from the condensation of the CH‐acidic cinnamic acid derivatives 19 with dimethylformamidedimethylacetal. CH and NH‐acidic compounds as cyanacetamide react with the aminals 3c,e exclusively with the acidic methylene group to produce the enamines 10h,t. The acylformamidine 21 can be obtained from 10t and tert‐butylaminalester 5. The pyridone 22 is accessible from the condensation product 10h by thermal cyclization. The pyrido[2,3‐d]pyrimidine 26 is formed in the reaction of the 6‐amino‐uracile 23 with the aminal 3a. In an unexpected reaction the 1,2‐bis(cyano‐dialkylaminomethylene)‐cyclobutanes 28a–d result from the action of trimethylsilylcyanide on the aminals 3e–h. The corresponding reaction with trimethylsilylisothiocyanate affords the vinylogous amidinium thiocyanates 34a, b. In the reaction of trimethylsilylazide and the aminals 3 are produced the 4‐(dialkylaminomethylene)‐4H‐1,2,3‐triazoles 38.

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Orthoamide. L. Beiträge zur Chemie von Propiolaldehydaminalen - Synthesen und Umsetzungen zu Push-Pull-substituierten Buta-1,3-dienen, Cyclobutanen sowie vinylogen Amidiniumsalzen und 1,2,3-Triazolen

1997

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“…Its treatment with ammonia gave rise to 1-amino-7,8,9,10-tetrahydropyrimido [4,5-h ] [1,6]naphthyridine (206). 126 Diazotisation of the amine of the naphthyridine series 207 with a of sodium nitrite in 10% H 2 SO 4 afforded naphthyridinone 208, which was used as the starting compound in the synthesis of the antagonist of benzodiazepine receptors 209. 127 ± 129 The compounds 210, including 1,6-naphthyridine derivatives, as well as octahydronaphthyridines 211 are of interest from the pharmacological standpoint.…”

Section: N Cophmentioning

confidence: 99%

Pyridopyridines

Литвинов¹,

Roman²,

Dyachenko³

2001

Russ. Chem. Rev.

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“…In this connection, we attempted to conduct the reaсtion of enaminodinitrile 5 with dimethylformamide diethyl aсetal (6) in the presenсe of a сatalyst, whiсh was chosen to be AlСl 3 (see Ref. 6).…”

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“…1 Н NMR spestra of sompounds 12, 14, and 15 in DMSO d6 Si as the internal standard. Mass spectra were recorded on a SSQ 710 Finnigan MAT instrument with direct inlet of a sample into the source of ions (ionizing voltage was 70 eV, temperature of the ionizing chamber was 150 °C) and on a Waters Miсromass ZQ 2000 instrument in the ESI+ regime.…”

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New synthesis of pyrido[4,3-b]indoles (γ-carbolines) on the basis of indolin-2-one lactim ether

et al. 2008

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Сondensation of indolin 2 one (oxindole) lactim ether with malononitrile leads to 2 diсyanоmethylidene 2,3 dihydroindole, the reaсtion of whiсh with dimethylformamide diethyl aсetal (or with triethyl orthoformate) and the subsequent сyсlization afford 4 сyanоpyrido[4,3 b]indoles (γ сarbоlines). 3 Amino 4 сyanоpyrido [4,3 b]indole was used in the synthesis of substi tuted pyrimido[4,5 c] γ сarbоlines.

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Synthesis of 7a,8,9,10-tetrahydro-2,3,5,6,7a-pentaazapyrene

Cited by 3 publications

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Orthoamide. L. Beiträge zur Chemie von Propiolaldehydaminalen - Synthesen und Umsetzungen zu Push-Pull-substituierten Buta-1,3-dienen, Cyclobutanen sowie vinylogen Amidiniumsalzen und 1,2,3-Triazolen

Orthoamide. L. Beiträge zur Chemie von Propiolaldehydaminalen - Synthesen und Umsetzungen zu Push-Pull-substituierten Buta-1,3-dienen, Cyclobutanen sowie vinylogen Amidiniumsalzen und 1,2,3-Triazolen

Pyridopyridines

New synthesis of pyrido[4,3-b]indoles (γ-carbolines) on the basis of indolin-2-one lactim ether

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