2,3,4,5‐Tetrahydropyridine Trimer

Claxton, G. P.; Allen, L. S.; Grisar, J. M.

doi:10.1002/0471264180.os056.25

Cited by 7 publications

(8 citation statements)

References 16 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Three different methods for generating ∆ 1 -piperideine were attempted: treatment of lysine with NBS, [7] dehydrohalogenation of N-chloropiperidine [8] and detrimerisation of α-tripiperideine (10). [9] Numerous assays were carried out to study the influence of different parameters -such as temperature, proportion of reactants, method of formation of 9 and pH -on the outcomes of the reactions. The best yield (34 %) of the lactam ester 11 (Scheme 1) was obtained by generation of 9 by slow detrimerisation of α-tripiperideine in water at pH 11 and simultaneous addition of DEM (2 equiv.).…”

Section: Synthesis Of the Key Intermediates 8 And 11mentioning

confidence: 99%

See 1 more Smart Citation

Synthesis of New Analogues of the Tetraponerines

Rouchaud

Braekman

2009

Eur J Org Chem

View full text Add to dashboard Cite

To evaluate the influences of the tetraponerine alkyl chains and tricyclic ring systems on their cytotoxic activities, we have prepared a series of alkyl derivatives (3a, 3b and 4a–f) of the non‐natural tricyclic skeletons decahydro‐2H,6H‐dipyrido[1,2‐a:1′,2′‐c]pyrimidine (3, 6–6–6 skeleton) and dodecahydro‐2H‐1,8a‐diazaphenanthrene (4, iso‐6–6–6 skeleton). In this study, two ways to synthesise the 6–6–6 analogues have been developed and compared. One is based on the condensation of α‐tripiperideine with diethyl malonate (DEM) in water at pH 11. This yielded oxo ester 11, precursor of the amino nitrile 8, but only in moderate yield. In the second pathway, the key intermediate 8 was more efficiently synthesised by starting from 2‐(2‐piperidyl)ethanol. Treatment of 8 with alkyl Grignard reagents led to the 6–6–6 analogues 3a and 3b. When the one‐pot reaction between α‐tripiperideine and DEM was performed in water at pH 8, the lactam 12, precursor of the iso‐6–6–6 skeleton, was obtained in a yield of 76 %. The same lactam was also obtained in a yield of 86 % by treatment of tetrahydroanabasine 14 with DEM in water at pH 8. Lactam 12 was transformed into the iso‐6–6–6 analogues 4a–4f. The cytotoxic activities of the 6–6–6 and iso‐6–6–6 analogues against HT29 cancer cells were compared with those of the 5–6–5 and 6–6–5 tetraponerines and with those of solenopsin analogues. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2009)

show abstract

Section: Synthesis Of the Key Intermediates 8 And 11mentioning

confidence: 99%

“…α-Tripiperideine (10): α-Tripiperideine was prepared according to the procedure of Claxton et al, [9] starting from a solution of Nchloropiperidine prepared as described above. This solution was added dropwise to a boiling solution of KOH (85 %, 2 g, 30.32 mmol) in absolute ethanol (32 mL).…”

mentioning

confidence: 99%

Synthesis of New Analogues of the Tetraponerines

Rouchaud

Braekman

2009

Eur J Org Chem

View full text Add to dashboard Cite

show abstract

“…In this step, low yields were observed when excessive heating was used for solvent removal because of the low boiling point of compound 8 . Δ 1 -piperidein was then crystalized out in its trimeric form as tripiperidein 9 in cold acetone ( Scheme 1 ) [ 11 ].…”

Section: Resultsmentioning

confidence: 99%

Total Synthesis of Novel Skeleton Flavan-Alkaloids

Jing

Simon

2020

Molecules

View full text Add to dashboard Cite

The first total synthesis of novel skeleton natural compounds kinkeloids A and B, a group of newly discovered flavan alkaloids isolated from the African plant Combretum micranthum, are described in this study. The key and final step are achieved by Mannich reaction, through which the piperidine moiety couples to the flavan moiety. The identities of synthesized kinkeloids were further confirmed through a comparison with the ones in the plant leaves extract using LC/MS.

show abstract

“…For more details about the properties of the trimer 3, its isolation methods, and its purification, see [132,[159][160][161] In chemical transformations the trimer 3 acts like a latent form of aminobutyraldehyde [33,162,163]. Early methods for the synthesis of the trimer 3 involved the reaction of pyrrolidine and tetramethylenediamine with hypochlorites by a modification of the procedure in [164] and also hydrolysis by a methanol solution of 1-formyl-2-methoxypyrrolidine hydrochloride (44% a of 3 together with 16% a of aminobutanal dimethyl acetal) [165]. A method with oxidation of pyrrolidine in an aqueous alkaline medium with sodium persulfate has preparative significance [159,166].…”

Section: -Phthalimidobutanalmentioning

confidence: 99%

“…NaOCl, NaOH base d a) XCl = NaOCl; base = NaOMe, 35% а 3 [160]; b) XCl = t-BuOCl, N-chlorosuccinimide, NaOCl, Ca(OCl) 2 ; base = KOH in MeOH [164,162] 1.4.2. 2-Hydroxy-and 1-Acyl-2-alkoxypyrrolidines.…”

Section: -Phthalimidobutanalmentioning

confidence: 99%