On attempted Diels-Alder reaction of 1-ethoxycarbonylindole-3- carboxaldehyde ,-dimethylhydrazone

Biswas, Goutam; Nath, A.; Mukherjee, Barid B.; Patra, Amarendra; Chakrabarty, Manas

doi:10.1016/s0040-4039(00)77689-1

Cited by 16 publications

(6 citation statements)

References 6 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…8 ± 11, 31, 33 ± 37 The C = C double bond of the 1-azadiene system of hydrazone may form a part of a carbocyclic moiety or a heterocycle. 8,33,45,61,62 Thus, reaction between cyclohex-1enecarbaldehyde hydrazone (21) and 2-bromo-8-hydroxynaphthalene-1,4-dione is used to obtain angular tetracyclic quinones 22 (Scheme 10). 45 …”

Section: Methodsmentioning

confidence: 99%

See 1 more Smart Citation

Hydrazones as substrates for cycloaddition reactions

Belskaya¹,

Eliseeva²,

Бакулев³

2015

Russ. Chem. Rev.

View full text Add to dashboard Cite

Section: Methodsmentioning

confidence: 99%

“…61,62 However, no cycloaddition products are observed for maleic anhydride, naphthoquinone and DMAD.…”

Section: Scheme 10mentioning

confidence: 99%

Hydrazones as substrates for cycloaddition reactions

Belskaya¹,

Eliseeva²,

Бакулев³

2015

Russ. Chem. Rev.

View full text Add to dashboard Cite

“…Further elimination of MeOH and, for 115, dehydrogenation, gave aromatic g-carboline derivatives 116a, -b, and 119 [151]. Annelated g-carboline 116c was also prepared in 30% yield by a Diels-Alder reaction of 120 and N-methylmaleimide in refluxing xylene (Scheme 38) [152].…”

Section: Scheme 34mentioning

confidence: 99%

Carbolines. Part I: Comparison of some methods for the synthesis of α-, γ-, and δ-carbolines (a review)

Smirnova¹,

Golovko²,

Граник³

2011

Pharm Chem J

View full text Add to dashboard Cite

The main trends in the development of the chemistry of a-, g-, and d-carbolines are generalized. Syntheses of carbolines based on pyridine derivatives (including the Fischer synthesis, Graebe-Ullmann reaction, thermal decomposition of azides, photochemical cyclization of anilinopyridines, arylation of substituted pyridines and piperidones, etc.) and based on indole derivatives are described. Published data about the biological activity of compounds belonging to these series are summarized.Four classes of pyridoindoles, i.e., carbolines (1 -4), are known. Of these, b-carbolines (2) have been studied most completely. Numerous studies, including several reviews [1 -3], have addressed the synthesis and various properties of this class of compounds. The properties of the other carbolines have been studied in less detail, e.g., their syntheses and chemical and physicochemical properties have not yet been discussed and compared in the literature.A detailed comparison seems especially important because precisely such an analysis can expose the basic features that make these classes chemically and biologically significant. This is especially important during research directed at the discovery of new biologically active compounds. Because the large volume of literature dedicated to b-carbolines makes it practically impossible to discuss it in a single review, the present review is limited to a comparison of the other carbolines only, the syntheses of which have been discussed much less in the literature. We intend to discuss the main trends in the development of the chemistry of a-, g-, and d-carbolines without pretending to include all literature in its entirety in order to compare the potential of finding novel effective drugs in these series. We discuss first reviews dedicated to pyridoindoles [2 -5], including a rather recent review of g-carbolines [6]. Then we switch to chemical approaches to the synthesis of selected carboline derivatives, noting briefly publications on their biological properties.Pyridoindoles (carbolines), including pyrido[4,3-b]indoles (g-carbolines), some of which exhibit a broad spectrum of biological activity, are definitely interesting. Drugs of this class already exist, e.g., neuroleptic carbidine 5 (Carbidinum or Stobadine) and dimebon antihistamine drugs 6 (Dimebonum) and diazoline 7 (Diazolinum or Omeril) [7,8]. Furthermore, dimebon exhibited pronounced anti-NMDA (N-methyl-D-asparate, ED 50 = 42 mg/kg i.p.) and anticalcium activity (blocks calcium channels, IC 50 = 57 mM) and inhibited acetylcholinesterase (ACE) and butyrylcholinesterase (BuCE) (IC 50 = 42 and 7.9 mM, respectively) in in vitro tests. It also had pronounced cognitive-stimulant properties in in vivo tests for a neurotoxic 654 0091-150X/11/4412-0654

show abstract

“…Of the many dienes used in synthesis 1-azadienes constitute an important class of compounds, among which 1-aza-1,3-dienes with a C=C bond that is part of a heteroarene are of particular interest for the production of condensed heterocyclic systems [68,69]. An example of such a structure is the N,N-dimethylhydrazone of 1-ethoxycarbonyl-3-formylindole, which readily enters into [4+4] cycloaddition with such a electron-deficient dienophile as N-methylmaleimide [70]. The formation of the γ-carboline is accompanied by the successive elimination of a dimethylamine molecule and dehydrogenation.…”

mentioning

confidence: 99%

“…The analogous transformation but with a smaller yield takes place for 1-benzoyl-3-formylindole N,N-dimethylhydrazone in the presence of catalytic amounts of p-toluenesulfonic acid [71]. It is interesting to note that the hetero Diels-Alder reaction does not occur if diethyl azodicarboxylate is used as electron-deficient dienophile, but 3-cyano-1-ethoxycarbonylindole is formed as a result of the elimination of a dimethylamine molecule from the initial compound participating in the reduction of the azodicarboxylate to N,N′-diethoxycarbonylhydrazine [70]. There are examples of the use of an intramolecular hetero-Diels-Alder reaction for the production of analogs of γ-carboline alkaloids 30 and 31 [72].…”

mentioning

confidence: 99%