Synthesis of Zwitterionic Compounds:  Fully Saturated Pyrimidinylium and 1,3-Diazepinylium Derivatives via the Novel Rearrangement of 3-Oxobutanoic Acid Thioanilide Derivatives

Zaleska, Barbara; Bazanek, Tomasz; Socha, Robert P.; Karelus, Marcin; Grochowski, J.; Serda, Paweł

doi:10.1021/jo025602a

Cited by 16 publications

(11 citation statements)

References 17 publications

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“…14 Studies on the synthesis of fully saturated heterocyclic systems have been our subject of interest. 15,16 In previous work 17 we have described a novel ring expansion of 1,3-diazines to 1,4-diazines resulting in piperazin-3-one and perhydroquinoxalin-3-one derivatives (Scheme 1).…”

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confidence: 99%

Synthesis of Saturated Imidazolidin[1,5-a]- and Thiazolidin[3,4-a]perhydroquinoxalin-4-one and Imidazolidin[1,5-a]piperazin-4-one Derivatives. Ring Contraction of Perhydroquinoxalin-4-one to Perhydrobenzimidazolin-2-one

Zaleska¹,

Socha²,

Karelus³

et al. 2004

Synthesis

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S y n t h e s i s o f S a t u r a t e d I m i d a z o l i d i n [ 1 , 5 -a ] F u s e d S y s t e m sAbstract: Saturated fused systems such as imidazolidin[1,5-a]-and thiazolidin[3,4-a]perhydroquinoxalin-4-one as well as imidazolidin[1,5-a]piperazin-4-one derivatives were prepared by cyclocondensation reactions of appropriate perhydroquinoxalin-3-one and piperazin-3-one derivatives with diiodomethane and thiophosgene. An unusual ring contraction of perhydroquinoxalin-3-one derivatives to perhydrobenzimidazolidin-2-one derivatives by reaction with 1,2-dibromoethane was proved using crystal structure analysis with synchrotron and laboratory radiation sources.

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confidence: 99%

Synthesis of Saturated Imidazolidin[1,5-a]- and Thiazolidin[3,4-a]perhydroquinoxalin-4-one and Imidazolidin[1,5-a]piperazin-4-one Derivatives. Ring Contraction of Perhydroquinoxalin-4-one to Perhydrobenzimidazolin-2-one

Zaleska¹,

Socha²,

Karelus³

et al. 2004

Synthesis

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“…7,8 Technical applications of ionic liquids present big diversity including preparation of photosensitizers, 9 solar cells, 10,11 lubricants for steel, 12,13 improvement of aerogels production 14 and HPLC methods, 15 and even embalming and tissue preservation for biological purposes. 16 We have already investigated 2-anilino-2-methoxy-3-oxothiobutanoic acid anilides 1a-c in the synthesis of various heterocyclic systems 17,18 and found unusual rearrangement leading to water soluble zwitterionic compounds 2, 3 with perhydropyrimidine and 1,3-diazepine moiety (Scheme 1) when 1,3-and 1,4-diamine were used. The structures of these compounds were confirmed by X-ray analysis of 2.…”

Section: Introductionmentioning

confidence: 99%

Perhydropyrimidinylium and 1,3-diazepinylium salts as potential ionic liquids

Zaleska¹,

Karelus²,

Flasiński³

et al. 2006

Arkivoc

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Saturated or partially saturated heterocyclic compounds were uncovered as interesting and potential ionic liquid media. Zwitterionic compounds with perhydropyrimidinylium, 1,3-diazepinylium and quinazolinylium carbocations were utilized in the preparation of a variety of salts in order to search for new low-melting ionic media. Some of the zwitterionic quinazoline derivatives were also found to be low-melting glasses.

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“…Products of such type of reaction had proven useful as good building blocks for constructing various heterocyclic systems. 7,8 N-(2¢-Pyridinyl)acetoacetamide (1) furnished the expected product 3a, in contrast to the reaction of N-(2¢-pyridinyl)benzoylacetamide (2) with nitrosobenzenes. This reaction unexpectedly afforded pyrido[1,2-a] [1,3,5]triazin-2-ones 4a-c (Scheme 1).…”

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confidence: 99%

“…This compound has got capacity to react as bielectrophilic system on C-2 in various ways, depending on reagents and reaction conditions, and usually leading to heterocyclic systems by new rearrangements. 7,8 These results encouraged us to undertake a study on the reactivity of N-(2¢-pyridinyl)acetoacetamide (1) and N-(2¢-pyridinyl)benzoylacetamide (2) with nitrosobenzenes. Products of such type of reaction had proven useful as good building blocks for constructing various heterocyclic systems.…”

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confidence: 99%

One-Pot Synthesis of 3,4-Dihydro-2H-pyrido[1,2-a][1,3,5]triazin-2-one Derivatives fromN-(2′-Pyridinyl)benzoylacetamide and Nitrosobenzenes

Zaleska¹,

Trzewik²,

Stodolak³

et al. 2004

Synthesis

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S y n t h e s i s o f 3 , 4 -D i h y d r o -2 H -p y r i d o [ 1 , 2 -a ] [ 1 , 3 , 5 ] t r i a z i n -2 -o n e sAbstract: A convenient method leading to fused pyrido[1,2-a] [1,3,5]triazine-2-ones is described. It consists in a one-pot, two-step reaction of N-(2¢-pyridinyl)benzoylacetamide with nitrosobenzenes. On the other hand, N-(2¢-pyridinyl)acetoacetamide provides a C-2 condensation/addition product with nitrosobenzene. N-(2¢-Pyridinyl)benzoylthioacetamide and N-(2¢-pyridinyl)acetothioacetamide with nitrosobenzene undergo oxidative heterocyclisation leading to [1,2,4]thiadiazolo[2,3-a]pyridine derivatives.The interest in the pyrido[1,2-a][1,3,5]triazine system arises from its wide biological activity, 1,2 which comes from its antagonistic effect upon 5-HT 2 and 5-HT 2a serotonin receptors. Such influence can result in: mediating coronary blood flow, 1a decreasing mean arterial blood pressure, 1b and the anti-thrombotic effect 1c in mammals. Other disorders, for whose prophylactic or therapeutic treatment pyrido[1,2-a][1,3,5]triazine derivatives can be used, are those involving airway constriction in human or animals: asthma, emphysema, chronic bronchitis, chronic obstructive pulmonary disease, 2 and various psychotic conditions including schizophrenia, depression, anorectic or bulimic eating disorders, and anxiety in humans. 2c Since 1952, when a possible approach to this system was mentioned for the first time, 3a several general methods of synthesis of pyrido[1,2-a][1,3,5]triazines have been invented, mostly leading to their oxo derivatives.Cyclodimerisation of iso(thio)cyanates leads to pyrido[1,2-a][1,3,5]triazine-2,4-di(thi)ones. 3b-d The other methods include: reaction of isocyanates 4a or active esters of imidodicarbonic 4b or carbonic 4c acid with 2-aminopyridine or other amidines and cyclisation of (thio)urea derivatives 3a or their reaction with isothiocyanate. 4d Pyrido[1,2-a][1,3,5]triazine-4-ones can be obtained from urea derivatives, 5a,b e.g. by their cyclisation, 5a or reaction of aryl isocyanates and unsymmetrical carbodiimides containing 2¢-pyridine ring. 5c,d There are only a few examples of the syntheses of pyrido[1,2-a][1,3,5]triazine-2-(thi)ones known. 3d,6

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Synthesis of Zwitterionic Compounds: Fully Saturated Pyrimidinylium and 1,3-Diazepinylium Derivatives via the Novel Rearrangement of 3-Oxobutanoic Acid Thioanilide Derivatives

Cited by 16 publications

References 17 publications

Synthesis of Saturated Imidazolidin[1,5-a]- and Thiazolidin[3,4-a]perhydroquinoxalin-4-one and Imidazolidin[1,5-a]piperazin-4-one Derivatives. Ring Contraction of Perhydroquinoxalin-4-one to Perhydrobenzimidazolin-2-one

Synthesis of Saturated Imidazolidin[1,5-a]- and Thiazolidin[3,4-a]perhydroquinoxalin-4-one and Imidazolidin[1,5-a]piperazin-4-one Derivatives. Ring Contraction of Perhydroquinoxalin-4-one to Perhydrobenzimidazolin-2-one

Perhydropyrimidinylium and 1,3-diazepinylium salts as potential ionic liquids

One-Pot Synthesis of 3,4-Dihydro-2H-pyrido[1,2-a][1,3,5]triazin-2-one Derivatives fromN-(2′-Pyridinyl)benzoylacetamide and Nitrosobenzenes

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