Convenient novel syntheses of 1,1-bis(heteroaryl)alkanes

Katritzky, Alan R.; Xie, Linghai; Fan, Wei

doi:10.1021/jo00068a036

Cited by 48 publications

(23 citation statements)

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“…[2][3][4][5] However, the synthesis of symmetric bis(2-furyl)methanes is still an important and challenging goal. The availability of these compounds continues to be of interest because they are industrially important.…”

Section: Introductionmentioning

confidence: 99%

(Aryl)(2-furyl)alkanes and their derivatives, 20. Synthesis of symmetric bis- and tris(2-furyl)methanes

Строганова¹,

Бутин²,

Sorotskaya³

et al. 2000

Arkivoc

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New methods for the synthesis of symmetric 5,5'-disubstituted bis-and 5,5',5"-trisubstituted tris(2-furyl)methanes have been developed. Symmetric bis(2-furyl)methanes were prepared from 5-substituted 2-furylmethanols in the presence of concentrated perchloric acid. The attempted synthesis of (aryl)[bis(2-furyl)]methanes from (aryl)(2-furyl)methanols in the presence of acid catalysts failed. The reaction of 5-substituted 2-furaldehydes with ethylene glycol in the presence of strong acid catalysts led to tris(2-furyl)methanes. Plausible mechanisms of these transformations are discussed.

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Section: Introductionmentioning

confidence: 99%

(Aryl)(2-furyl)alkanes and their derivatives, 20. Synthesis of symmetric bis- and tris(2-furyl)methanes

Строганова¹,

Бутин²,

Sorotskaya³

et al. 2000

Arkivoc

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“…Elemental analyses were performed on a Vario‐ELIII instrument. Compounds 1 were prepared using the method analogous to that for the preparation of benzyloxycarbonylamino‐1‐(1‐benzotriazolyl)alkanes [8].…”

Section: Methodsmentioning

confidence: 99%

Selective substitution reactions of methoxycarbonylamino‐1‐(1‐benzotriazolyl)alkanes with active methylene compounds

Zhou

Mao

et al. 2011

Journal of Heterocyclic Chem

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Benzotriazole adducts methoxycarbonylamino‐1‐(1‐benzotriazolyl)alkanes 1 were derived from the condensation of an aldehyde, benzotriazole, and methylcarbamate. The leaving tendency of methoxycarbonylamino group (MeOCONH) and benzotriazole group (Bt) was investigated by treatment of the adducts with active methylene compounds under either Lewis acid‐catalyzed or basic conditions. In the presence of SmI3, MeOCONH take priority over Bt in the leaving process, whereas in the presence of MeONa, the Bt was substituted in preference. Thus, the tunable substitution of the two leaving groups could be used for different synthetic purposes. J. Heterocyclic Chem., 00, 00 (2011).

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“…Recently, much attention has been directed toward the synthesis of bis(heterocyclyl)methanes because of their diverse biological and pharmacological activities. [7][8][9][10][11][12][13] Bis(heterocyclyl) methanes constitute building blocks in natural and unnatural porphyrins. 14 Because of their biological activity, several different methods have been developed, such as Amberlyst 15, 15 Zn(Proline) 2 , 16 Montmorillonite clay, 17 InCl 3 , 18 TiO 2 /SO 4 , 19 phosphomolybdic acid 20 and ethyl ammonium nitrate (EAN).…”

Section: Introductionmentioning

confidence: 99%

Pd(0) NPs: a novel and reusable catalyst for the synthesis of bis(heterocyclyl)methanes in water

2012

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Convenient novel syntheses of 1,1-bis(heteroaryl)alkanes

Cited by 48 publications

References 0 publications

(Aryl)(2-furyl)alkanes and their derivatives, 20. Synthesis of symmetric bis- and tris(2-furyl)methanes

(Aryl)(2-furyl)alkanes and their derivatives, 20. Synthesis of symmetric bis- and tris(2-furyl)methanes

Selective substitution reactions of methoxycarbonylamino‐1‐(1‐benzotriazolyl)alkanes with active methylene compounds

Pd(0) NPs: a novel and reusable catalyst for the synthesis of bis(heterocyclyl)methanes in water

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