Synthesis and biological activity of pyrrole, pyrroline and pyrrolidine derivatives with two aryl groups on adjacent positions

Bellina, Fabio; Rossi, Renzo

doi:10.1016/j.tet.2006.05.024

Cited by 586 publications

(157 citation statements)

References 401 publications

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“…[44][45][46][47][48][49][50][51][52][53][54][55][56][57][58][59] Aryl and heteroaryl-annulated carbazoles, such as pyridocarbazoles, indolocarbazoles, and pyrrolocarbazoles have attracted growing attention since they are distributed in numerous natural products with diverse useful bioactivities. [60][61][62][63][64][65][66][67][68] Aminocarbazoles have been an important synthon to construct pyridocarbazoles, 69 which are well known for their antitumor properties. 70,71 Also, aminocarbazoles have been used to prepare pyrimido [5,4-b]carbazole derivatives.…”

Section: Introductionmentioning

confidence: 99%

Applications of aminocarbazoles in heterocyclic synthesis

Reddy¹,

Padmaja²

2015

Arkivoc

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Aminocarbazoles are versatile building blocks in organic synthesis. This review focuses on the application of aminocarbazoles to generate a large variety of fused carbazole heterocycles such as pyridocarbazoles, isomeric pyridocarbazoles, thiazolocarbazoles, pyrimidocarbazoles, pyrrolocarbazoles, indolocarbazoles, quino-and chromeno-carbazoles and many others. Many of these molecules exhibit promising biological activities.

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Section: Introductionmentioning

confidence: 99%

Applications of aminocarbazoles in heterocyclic synthesis

Reddy¹,

Padmaja²

2015

Arkivoc

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“…2 Moreover, optically active pyrrolidine-containing compounds derived from proline are with fundamental importance for the preparation of most efficient ligands and organocatalysts. 3 However, relatively little is known about the synthesis and applications of enantiomerically pure bis-heterocycles containing the pyrrolidine ring.…”

Section: Introductionmentioning

confidence: 99%

Synthesis of optically active polycyclic N-heterocycles derived from l-prolinamine1

Wróblewska

Mlostoń

Heimgartner

2015

Tetrahedron: Asymmetry

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The N-Boc-protected (S)-prolinamine reacts readily with formaldehyde and diverse alphahydroxyimino ketones to give imidazole N-oxides with an enantiomerically pure N-protected (pyrrolidin-2-yl)methyl substituent. Subsequent deprotection yields the corresponding NH derivatives. Upon treatment of these products with Ac2O at room temperature, a cascade of reactions leads to optically active tricyclic products. In all these processes, the stereogenic center is preserved. In one case, the bis-heterocyclic imidazole N-oxide was transformed into the corresponding optically active imidazole-2-thione via a sulfurtransfer reaction with 2,2,4,4-tetramethylcyclobutane-1,3-dithione. E-mail addresses: anetka.wroblewska@gmail.com (A. Wróblewska).1 AbstractThe N-Boc-protected (S)-prolinamine reacts easily with formaldehyde and diverse α-hydroxyimino ketones to give imidazole N-oxides with an enantiomerically pure Nprotected (pyrrolidin-2-yl)methyl substituent. Subsequent deprotection yields the corresponding NH derivatives. Upon treatment of these products with Ac 2 O at room temperature, a cascade of reactions leads to optically active tricycyclic products. In all these processes, the stereogenic centre is preserved. In one case, the bis-heterocyclic imidazole N-oxide was transformed to the corresponding optically active imidazole-2-thione via the sulfur-transfer reaction with 2,2,4,4-tetramethylcyclobutane-1,3-dithione.

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“…Photolysis of 1-substituted benzotriazoles 1a,b to indoles and benzimidazoles However, literature survey indicated that little investigation have been made on thermolytic and/or photolytic behavior of 1-alkenyl-substituted-1,2,3-triazoles (Boyer & Silvarajan, 1969;Burgess, Carithers, & McCullagh, 1968;Michell & Rees, 1987;Ogata, Takaji, & Hayashi, 1977;Silvarajan & Boyer, 1972;Wender & Cooper, 1969). In the light of the established pharmaceutical activity of 3-dimethylaminopyrrole which is reported as an analgesics and anticonvulsants agent (Bellina & Rossi, 2006;Rochais, Lisowski, Dallemagne, & Rault, 2004; Liebscher et al, 1992) we became interested in developing photoinduced synthetic route to such compounds via photolysis of suitably 1-substituted-1,2,3-triazole.…”

Section: Introductionmentioning

confidence: 99%