Synthesis and 13C, 15N NMR study of a new functionalized pyrido[2,3‐b]indole derivative

Buisson, Jean‐Pierre; Bisagni, Émile; Monneret, Claude; Demerseman, P.; León, Claudia de; Platzer, N.

doi:10.1002/jhet.5570330368

Cited by 5 publications

(5 citation statements)

References 21 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…No trace of diazepine compounds was detected. For compound 43 (CDCl 3 , 0.15 equiv of chromium(III)acetylacetonate), the resonances obtained at δ 128 (N(10)), 166 (N(5)), and 189 (N(1)) confirm the pyridinone form 31 also favored by the ester group . The complete structural analysis of 43 was established by INEPT experiments, in which the long-range interactions of H(2) with carbons C(3) (106.8), C(4) (161.0), CO 2 Et (170.3), and C(10a) (145.2) were identified.…”

Section: Resultsmentioning

confidence: 97%

“…1, 34.5, 56.7, 113.0, 114.3, 119.2, 120.5, 125.0, 131.2, 135.0, 139.4, 145.5, 163.7, 168.8 4, 14.8, 36.7, 61.4, 106.3, 108.4, 113.5, 114.8, 124.5, 129.1, 132.9, 141.8, 144.1, 154.5, 165.8; MS m/z 284 (M + , 100), 256 (35), 195 (24), 184 (39) 13 C NMR (CDCl3) δ 14.4, 15.0, 36. 1, 61.5, 106.6, 110.1, 112.5, 114.1, 126.7, 131.5, 135.8, 141.8, 144.5, 155.3, 166.2; MS m/z 284 (M + , 37), 255 (23), 210 (90), 195 (41), 182 (37), 149 (32), 69 (76), 57 (100). Anal.…”

Section: Methodsmentioning

confidence: 99%

“…5-Ethoxycarbonyl-3-(N-ethylamino)pyrido[6,1,2-cd]-2,3a,7-triazaazulene (32): yield 42%; mp 139-141 °C; IR (KBr) 1715,1600,1555,1295,1265,1235,795, 740 cm -1 ; 1 H NMR (CDCl3) δ 1.35 (m, 6 H), 3.51 (q, 2 H, J ) 7 Hz), 4.30 (q, 2 H, J ) 7 Hz), 6.62 (d, 1 H, J ) 7 Hz), 7.14 (dd, 1 H, J ) 9, 7 Hz),7.48 (s,1 H),7.53 (d,1 H, J ) 9 Hz), 7.69 (s, 1 H); 13 C NMR (CDCl3) δ 14.2,15.5,62.7,109.5,111.5,115.3,124.6,133.6; MS m/z 284 (M + , 100), 209 (19),195 (46),169 (84),156 (23). Anal.…”

Section: Methodsmentioning

confidence: 99%

See 2 more Smart Citations

Heterocyclization of Functionalized Vinylic Derivatives of Imidazo[1,2-a]pyridines

et al. 2001

View full text Add to dashboard Cite

Heterocyclization of functionalized vinylic derivatives of imidazo[1,2-a]pyridines was explored experimentally and theoretically using semiempirical AM1 and ab initio methods. A range of functionalized vinylic derivatives (azido, amino, and carbodiimide groups) were prepared for conversion into pyrroloazaindoles 19-22, imidazo[1,x]-, (x = 5, 6, 7, 8), [2,6]-, and [2,7]naphthyridines 28-30, 35-38 by thermal reaction. In the case of vinylic groups in the 5 position, peri annulation also was observed. The experimental and theoretical data are compared and discussed.

show abstract

Section: Resultsmentioning

confidence: 97%

Section: Methodsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

See 1 more Smart Citation

Heterocyclization of Functionalized Vinylic Derivatives of Imidazo[1,2-a]pyridines

et al. 2001

View full text Add to dashboard Cite

show abstract

“…The derivatives of 4-hydroxy-2-pyridones exhibit a wide range of biological activities (Buisson et al, 1996;Jessen & Gademann, 2010). The title compound, C 13 H 15 NO 4 S, is an important intermediate in the synthesis of 4-hydroxy-2pyridone derivatives (Rigby & Burkhardt, 1986;Rigby & Qabar, 1989).…”

Section: S1 Commentmentioning

confidence: 99%

Ethyl (E)-3-hydroxy-2-{N-[2-(thiophen-2-yl)ethenyl]carbamoyl}but-2-enoate

Liu

Zhao

2012

Acta Cryst E

View full text Add to dashboard Cite

In the title compound, C13H15NO4S, there are two independent but conformationally similar molecules in the asymmetric unit, both having an E conformation of the side-chain C=C group. Intramolecular N—H⋯O and O—H⋯O hydrogen-bonding interactions are present in both molecules. In the crystal, one of the molecule types is linked through intermolecular hydroxy–ketone O—H⋯O interactions, forming one-dimensional chains extending along [010], whereas the other molecule type shows no associations.

show abstract

“…The signals for the aromatic protons of the indole frag ment in compound 3 were assigned using double homo nuclear resonance and published data. In particular, the doublet at δ 7.30 was assigned to the H(5) proton based on known data for indole, 9,10 pyrido[2,3 b]indol 2(1H ) one, 11 and benzopyrimido [4,5 b]indole 2,4(1H,3H ) dione 12 derivatives.…”

mentioning

confidence: 99%

Synthesis of 2-thio derivatives of 4-phenyl-9H-pyrimido[4,5-b]indole

2006

View full text Add to dashboard Cite

The reaction of 3 benzylidene 2 ethoxyindolenine tetrafluoroborate with thiourea gives a mixture of 4 phenylpyrimido [4,5 b]indole 2(1H ) thione, its 3,4 dihydro derivative, and the corresponding disulfide, the product ratio depending on the reaction conditions. A number of transformations of the resulting compounds, in particular, those giving 2 alkylthio pyrimido indole derivatives are described. Key words: 4 phenyl 9H pyrimido[4,5 b]indole 2(1H ) thione, 2 alkylthio derivatives of 4 phenyl 9H pyrimido[4,5 b]indole, alkylation, oxidation, nucleophilic substitution, desulfu rization.The functional derivatives of pyrimido[4,5 b]indole, in particular, synthetically most available 2 and 4 amino substituted derivatives, possess a broad spectrum of bio logical activities and present interest as a base for the development of new medicines. 1-3 The corresponding thio derivatives may also attract attention as biologically active substances, since compounds possessing antioxi dant, antihypoxic, and hepatoprotector activities have been found in the series of related heterocyclic systems, 1,2,4 triazino[5,6 b] and [6,5 b]indoles. 4-6 In order to extend the range of functional derivatives of 4 phenyl pyrimido[4,5 b]indole and to study their properties, we attempted to synthesize its 2 thio derivatives.Previously, we carried out the reaction of 3 ben zylidene 2 ethoxyindolenine tetrafluoroborate (1) with thiourea, which yielded a product identified as 4 phenyl pyrimido[4,5 b]indole 2,4(1H ) thione (2) 7 (Scheme 1). A repeated detailed study of the reaction showed that this product is actually a mixture of thione 2, its 3,4 dihydro derivative 3, and disulfide 4. Similar analytical and spec troscopic characteristics of compounds 2-4, their poor solubility in most organic solvents, similar chromato graphic behaviors of thiones 2 and 3, and easy transfor mation into disulfide 4 make separation and identifica tion of these compounds a difficult task. The presence of both thiones in the mixture can be detected by mass spec trometry, whereas disulfide 4 is not detected due to its very low volatility. All three components of the mixture can be observed by HPLC with mass selective detection (HPLC MSD). In addition, the presence of disulfide 4 can be determined by TLC.

show abstract

Synthesis and ¹³C, ¹⁵N NMR study of a new functionalized pyrido[2,3‐b]indole derivative

Abstract: New functionalized α‐carbolinones especially the 4‐hydroxy‐3‐nitro‐1H,9H‐pyrido[2,3‐b]indol‐2‐one were synthesized in a good yield, three‐step reaction. A complete 13C, 15N nmr study of this carbolinone and precursors is presented.

Cited by 5 publications

References 21 publications

Heterocyclization of Functionalized Vinylic Derivatives of Imidazo[1,2-a]pyridines

Heterocyclization of Functionalized Vinylic Derivatives of Imidazo[1,2-a]pyridines

Ethyl (E)-3-hydroxy-2-{N-[2-(thiophen-2-yl)ethenyl]carbamoyl}but-2-enoate

Synthesis of 2-thio derivatives of 4-phenyl-9H-pyrimido[4,5-b]indole

Contact Info

Product

Resources

About