Efficient Synthesis of 3-Arylphthalides†

Paradkar, M. V.; Ranade, Anup A.; Kulkarni, Madhuri S.; Godbole, Himanshu M.; Joseph, Augustine R.

doi:10.1039/a800804c

Cited by 10 publications

(5 citation statements)

References 7 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…A convenient synthesis of 6-acylcoumarins from 6-alkylcoumarins, was reported [99]. 7-Phenoxymethyl and 7-anilinomethyl coumarins were prepared by bromination of the methyl group of 7-methylcoumarin with Nbromosuccinimide [113].…”

Section: From Alkylcoumarinsmentioning

confidence: 99%

“…This synthetic route has been often used for obtaining natural coumarins and other benzopyrones with biological or industrial interest [9,[96][97][98][99][100][101][102][103][104][105][106][107][108][109][110][111][112]. To mention the interesting synthesis of a 7-trans-styrylcoumarin derivative, which was prepared by reacting ethyl 2-methylacetoacetate with 3-trans-styrylphenol [113].…”

Section: Perkin Reactionmentioning

confidence: 99%

See 1 more Smart Citation

Simple Coumarins and Analogues in Medicinal Chemistry: Occurrence, Synthesis and Biological Activity

Borges¹,

Roleira²,

Milhazes³

et al. 2005

CMC

882

458

View full text Add to dashboard Cite

Coumarins, also known as benzopyrones, are present in remarkable amounts in plants, although their presence has also been detected in microorganisms and animal sources. The structural diversity found in this family of compounds led to the division into different categories, from simple coumarins to many other kinds of policyclic coumarins, such as furocoumarins and pyranocoumarins. Simple coumarins and analogues are a large class of compounds that have attracted their interest for a long time due to their biological activities: they have shown to be useful as antitumoural, anti-HIV agents and as CNS-active compounds. Furthermore, they have been reported to have multiple biological activities (anticoagulant, anti-inflammatory), although all these properties have not been evaluated systematically. In addition, their enzyme inhibition properties, antimicrobial and antioxidant activities are other foremost topics of this field of research. The present work is to survey the information published or abstracted from 1990 till 2003, which is mainly related to the occurrence, synthesis and biological importance of simple coumarins and some analogues, such as biscoumarins and triscoumarins. Data are also highlighted, concerning the development of new synthetic strategies that could help in drug design and in the work on SAR or QSAR.

show abstract

Section: From Alkylcoumarinsmentioning

confidence: 99%

Section: Perkin Reactionmentioning

confidence: 99%

Simple Coumarins and Analogues in Medicinal Chemistry: Occurrence, Synthesis and Biological Activity

Borges¹,

Roleira²,

Milhazes³

et al. 2005

CMC

882

458

View full text Add to dashboard Cite

show abstract

“…For general background to isobenzofuran-1(3H)-ones, see: Landge et al (2008); Mukhopadhyay & Kundu (2001); Paradkar et al (1998).…”

Section: Related Literaturementioning

confidence: 99%

3,3′-Oxybi[isobenzofuran-1(3H)-one]

Yin

Wen

et al. 2009

Acta Cryst E

View full text Add to dashboard Cite

The title compound, C16H10O5, consists of two isobenzofuran-1(3H)-one moieties which are linked by a bridging O atom. The two halves of the molecule display approximate non-crystallographic mirror symmetry. The dihedral angle between the two isobenzofuran-1(3H)-one ring systems is 53.18 (6) Å. Two chiral carbon centres are observed in the compound, but their absolute configurations could not be determined. In the crystal structure, intermolecular C—H⋯O hydrogen bonds link molecules into zigzag chains along c. Additional C—H⋯O interactions connect adjacent chains.

show abstract

“…For general background to isobenzofuran derivatives, see: Landge et al (2008); Paradkar et al (1998); Joseph (1998). Odabaşog lu & Bü yü kgü ngö r (2008).…”

Section: Related Literaturementioning

confidence: 99%

“…Data collection: SMART (Siemens, 1996); cell refinement: SAINT (Siemens, 1996); data reduction: SAINT; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXTL. Phthalides (isobenzofuran-1(3H)-ones) are well known for their interesting biological properties (Paradkar et al, 1998;Joseph, 1998). In addition, 3-substituted phthalides are vital heterocyclic motifs in many bioactive compounds such as isocoumarins, anthraquinones, anthracyclines, and several alkaloids (Landge et al, 2008).…”

Section: Data Collectionmentioning

confidence: 99%