7-Chloro-2-[1-(4-methoxyphenyl)pyrazol-4-yl]-3,3-dimethyl-3H-indole

Abstract

In the title compound, C20H18ClN3O, the dihedral angle between the pyrazole and the 3H-indole components is only 13.28 (6)°, indicating that there is conjugation between the two heterocyclic subunits. The N-methoxy­phenyl unit makes a dihedral angle of 25.10 (7)° with the pyrazole ring.

2-[(Z)-4,7-Dichloro-3,3-dimethyl-2,3-dihydro-1H-indol-2-ylidene]-3-oxopropanenitrile

“…For related structures, see: Baradarani et al (2006); Helliwell et al (2010) Rashidi et al (2009). For the chemistry of complexes of (2H-indol-2-ylidene)propanedials, see: Rashidi et al (2011).…”

“…We showed that the interaction of 2,3,3-trimethyl-3H-indoles with the Vilsmeier reagent produces (1,3-dihydro-3,3-dimethyl-2H-indol-2-ylidene)propanedials (Baradarani et al, 2006) (Rashidi et al, 2009), 2,2′,3,3,3′,3′-hexamethyl-3H,3′H-5,5′-biindole and 2,3,3,7,8,8hexamethyl-3H,8H-indolo[7,6-g]indole (Rashidi et al, 2011) behave analogously. The (1,3-dihydroindol-2-ylidene)propanedials were shown to react with arylhydrazines (or hydrazine) to produce 3,3-dimethyl-2-[1-aryl-1Hpyrazol-4-yl]-3H-indoles (Baradarani et al, 2006;Rashidi et al, 2009;Helliwell et al 2010;Rashidi et al, 2011).…”

Synthesis of New Heterocyclic Compounds Using 2‐(3,3‐dimethyl‐1H‐pyrroloisoquinolin‐2(3H)‐ylidene)malonaldehydes

“…We recently described the reaction of indolenines 7 and some pyridoindolenines, with the Vilsmeier reagent formed from N,N ‐dimethylformamide and phosphorus oxychloride to produce aminomethylene malondialdehydes such as 8 . Additionally, we showed that these intriguing polyfunctional compounds reacted well with hydrazine or arylhydrazines to produce corresponding pyrazoles 9 , with migration of the exocyclic double bond back into the pyrrole ring, thus restoring the indolenine structure from which the sequence started (Scheme ).…”

The Synthesis of 6‐Substituted Pyrido[2,3‐d]pyrimidine‐2,4(1H,3H)‐diones Using Aminomethylene Malondialdehydes and 6‐Aminouracils

“…1 , is a general process, by demonstrating the transformation using variously substituted 2,3,3‐trimethyl‐3 H ‐indoles . Additionally, we have described a simple and straightforward preparation of 4‐(3,3‐dimethyl‐3 H ‐indol‐2‐yl)‐substituted pyrazoles 2 by condensation of these aminomethylene malondialdehydes with hydrazine and aryl hydrazines (Scheme ).…”