Synthesis of 4-Hydroxy-7,8-dimethoxyisochroman-3-one and Its Plant Growth-Regulating Properties on Tobacco (<i>Nicotiana tabacum</i> cv. Petit Havana)

In the title compound, C17H12O4, the six-membered heterocyclic ring adopts a distorted screw-boat conformation. The molecular structure exhibits an S(6) ring motif, owing to an intramolecular O—H⋯O hydrogen bond. In the crystal, weak C—H⋯O contacts generate an infinite chain along the c axis. There are also π–π stacking interactions between neighbouring isochromanedione benzene rings, with a centroid–centroid distance of 3.755 (1) Å, and C—O⋯π interactions with an O⋯centroid distance of 3.964 (2) Å.

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“…For the biological activity of isochromanones, see: Bianchi et al, (2004); Buntin et al (2008). Forstacking interactions, see: Janiak (2000).…”

Section: Related Literaturementioning

confidence: 99%

“…The title molecule is related to the isochromanone derivatives that are generally known as regulators of plant growth (Bianchi et al, 2004). Depending on their chemical structure and concentration they can act either as inhibitors or stimulators in these processes.…”

Section: S1 Commentmentioning

confidence: 99%

4-[(Hydroxy)(4-methylphenyl)methylidene]isochroman-1,3-dione

et al. 2011

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“…Isochroman constitutes an important structural motif widely encountered in natural products and in many biologically active compounds. Owing to its importance, several methods are reported in the literature for the synthesis of isochromans and isochromenes.…”

Section: Introductionmentioning

confidence: 99%

An Unprecedented Synthesis of 3,3‐Disubstituted Isochroman‐1,4‐diones Using Nitrones as Oxygen Atom Donors

Sathi

Deepthi

Thomas

2019

Journal of Heterocyclic Chem

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A one‐pot reaction of ninhydrin, N‐methyl‐C‐phenyl nitrone, and secondary amine leading to the unprecedented synthesis of 3,3‐disubstituted isochroman‐1,4‐diones is described here. In this reaction, nitrone acts as an oxygen atom donor producing an imine as a side product. The mild reaction conditions, the flexibility of the secondary amines that can be used, the novelty of the product, and the good yields are the highlights of this reaction.

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“…The antiplatelet activity and antioxidant power of these isochromans were also evaluated, and were found to be effective free radical scavengers and inhibited platelet aggregation and thromboxane release evoked by agonists [8]. 3,7-Dimethoxy-8-hydroxy-6-methoxyisochroman isolated from Penicillium corylophilium and its synthetic analogues exhibit plant growth regulatory and herbicidal activity [9].…”

Section: Introductionmentioning

confidence: 99%