ChemInform Abstract: SYNTHESIS AND PREGNANCY TERMINATING ACTIVITY OF 2‐ARYLPYRAZOLO(5,1‐A)ISOINDOLES AND ‐ISOQUINOLINES

Toja, E.; Omodei-Salè, A.; Cattaneo, C; Galliani, G.

doi:10.1002/chin.198239230

Cited by 7 publications

(9 citation statements)

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“…[181] Its gas-phase basicity has been studied, [9] which was correlated with calculated molecular electrostatic potential maps. Thus, antiallergic and cerebroactive compounds [193] have been found, and studies on inhibitory activity on platelet aggregation [194] as well as on pregnancy termination [195] have been reported. [191,192] Some of the derivatives of the title ring system exhibit valuable biological properties.…”

Section: Methods 3: Oxidationmentioning

confidence: 99%

“…Two benzo analogues of the title system, imidazo[5,1-a]isoquinoline (195) and imidazo[1,5-a]quinoline (197), have been synthesized by one simple step, though in modest yield (Scheme 34). The dilithio derivative of tosylmethyl isocyanide participates as a 1,3dipole in dipolar cyclization with isoquinoline (194) and quinoline (196) and yields the ring-closed products 195 and 197, respectively.…”

Section: Methods 2: 13-dipolar Cyclizationmentioning

confidence: 99%

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Product Class 5: Azaindolizines with Two Nitrogen Atoms in the Five-Membered Ring

Neier¹,

Bellus²

2002

Category 2, Hetarenes and Related Ring Systems

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In contrast to Section 12.5.1.1.1.1, where in most cases the first reaction step is the quaternization of a pyridin-2-amine derivative followed by nucleophilic attack of the 2-amino group on an appropriate functional group to form the imidazole ring, several ring closures have been elaborated starting from substituted pyridin-2-amines. In these cases, the â-carbon atom of the carbon chain attached to the 2-amino group bears an appropriate functional group, and a nucleophilic attack of the pyridine ring nitrogen atom at this center results in formation of the imidazole ring. Such syntheses are shown in Scheme 8.

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Section: Methods 3: Oxidationmentioning

confidence: 99%

Section: Methods 2: 13-dipolar Cyclizationmentioning

confidence: 99%

Product Class 5: Azaindolizines with Two Nitrogen Atoms in the Five-Membered Ring

Neier¹,

Bellus²

2002

Category 2, Hetarenes and Related Ring Systems

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“…The overall outcome of this reaction is to convert three C–H bonds to three C–C bonds, resulting in a pyrazolo[5,1- a ]isoquinoline framework in a step-economical manner with high efficiency. Pyrazoloisoquinolines are biologically important heterocycles that display pregnancy terminating activity and anti -reproductive properties . This relay visible light photoredox catalysis strategy will enrich the synthetic potential visible-light photoredox catalysis and enable more novel reaction modes.…”

mentioning

confidence: 99%

Relay Visible-Light Photoredox Catalysis: Synthesis of Pyrazole Derivatives via Formal [4 + 1] Annulation and Aromatization

Cheng

Duan

et al. 2016

Org. Lett.

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A relay visible-light photoredox catalysis strategy has been accomplished. Three successive photoredox cycles (one oxidative quenching cycle and two reductive quenching cycles) are engaged in a single reaction with one photocatalyst. This strategy enables formal [4 + 1] annulation of hydrazones with 2-bromo-1,3-dicarbonyl compounds, which functionalizes three C-H bonds of hydrazones. This method affords rapid access to a complex and biologically important pyrazole scaffold in a step-economical manner with high efficiency under mild conditions.

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“…Compound 1 was prepared directly according to a modified literature procedure . The precursor compounds 11 H -benzo[4,5]imidazo[2,1- a ]isoindole ( pre-2 ) and 2-phenyl-5 H -[1,2,4]triazolo[5,1- a ]isoindole ( pre-3 ) for 2 and 3 , respectively, were prepared according to literature procedures (see the Supporting Information).…”

mentioning

confidence: 99%

1,1-Hydroboration of Fused Azole–Isoindole Analogues as an Approach for Construction of B,N-Heterocycles and Azole-Fused B,N-Naphthalenes

et al. 2016

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Three isoelectronic analogues of pyrido[2,1-a]isoindole have been found to undergo a facile 1,1-hydroboration with HBMes2 borane, which provides a new and convenient method for the synthesis of B,N-heterocycles 1a-3a in high yields. Compounds 1a-3a can undergo photoelimination upon irradiation at 300 nm, generating heterocycle-fused B,N-naphthalene molecules 1b-3b, which display distinct yellow-green and blue fluorescent colors, respectively. Compound 1a undergoes thermal elimination, producing 1b at 280 °C, while compound 2a only undergoes partial elimination, forming 2b at 320 °C. Compound 3a is thermally stable up to 320 °C.

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ChemInform Abstract: SYNTHESIS AND PREGNANCY TERMINATING ACTIVITY OF 2‐ARYLPYRAZOLO(5,1‐A)ISOINDOLES AND ‐ISOQUINOLINES

Cited by 7 publications

References 0 publications

Product Class 5: Azaindolizines with Two Nitrogen Atoms in the Five-Membered Ring

Product Class 5: Azaindolizines with Two Nitrogen Atoms in the Five-Membered Ring

Relay Visible-Light Photoredox Catalysis: Synthesis of Pyrazole Derivatives via Formal [4 + 1] Annulation and Aromatization

1,1-Hydroboration of Fused Azole–Isoindole Analogues as an Approach for Construction of B,N-Heterocycles and Azole-Fused B,N-Naphthalenes

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