Vilsmeier-Haack Reaction with 2,3,3-Trimethyl-3H-benzo[g]indole and Its Conversion into 2-(1-aryl-1H-pyrazol-4-yl)-3,3-dimethyl-3H-benzo[g]indoles

Authors

  • Laya Roohi Department of Organic Chemistry, Faculty of Chemistry, University of Urmia, Urmia 57153-165, Iran
  • Mohsen Khezri Department of Organic Chemistry, Faculty of Chemistry, University of Urmia, Urmia 57153-165, Iran
Abstract:

Vilsmeier-Haack reaction of 2,3,3-trimethyl-3H-benzo[g]indole, then aqueous basic work-up, leads to benzo[g]indol-2-ylidene- malondialdehydes. These react with various arylhydrazines and quinolin-2-ylhydrazine to form 3,3-dimethyl-2-(1-aryl-1H-pyrazol-4-yl)- 3H-benzo[g]indoles in good yields.

Upgrade to premium to download articles

Sign up to access the full text

Already have an account?login

similar resources

vilsmeier-haack reaction with 2,3,3-trimethyl-3h-benzo[g]indole and its conversion into 2-(1-aryl-1h-pyrazol-4-yl)-3,3-dimethyl-3h-benzo[g]indoles

vilsmeier-haack reaction of 2,3,3-trimethyl-3h-benzo[g]indole, then aqueous basic work-up, leads to benzo[g]indol-2-ylidene- malondialdehydes. these react with various arylhydrazines and quinolin-2-ylhydrazine to form 3,3-dimethyl-2-(1-aryl-1h-pyrazol-4-yl)- 3h-benzo[g]indoles in good yields.

full text

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

In the title compound, C(20)H(18)ClN(3)O, 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-methoxy-phenyl unit makes a dihedral angle of 25.10 (7)° with the pyrazole ring.

full text

(±)-3-(5-Amino-3-methyl-1-phenyl-1H-pyrazol-4-yl)-2-benzo­furan-1(3H)-one

In the title compound, C18H15N3O2, the benzo-furan ring system is essentially planar, the rings making a dihedral angle of 0.57 (9)°. The phenyl, furan and benzene rings subtend dihedral angles of 47.07 (10), 85.76 (7) and 86.04 (7)°, respectively, with the pyrazole ring. In the crystal, mol-ecules are linked by weak N-H⋯N, N-H⋯O and C-H⋯O inter-actions, generating edge-fused R 4 (4)(20), and R...

full text

2,3,3-Trimethyl-1-[4-(2,3,3-trimethyl-3H-indol-1-ium-1-yl)but­yl]-3H-indol-1-ium diiodide

In the crystal of the title salt, C(26)H(34)N(2) (2+)·2I(-), the dication lies on a center of inversion that exists along the mid-point of the butyl chain; its five-membered ring is approximately planar (r.m.s. deviation = 0.011 Å). In the crystal, the iodide anion is disordered over two positions in a 1:1 ratio.

full text

(3,5-Dimethyl-1H-pyrazol-1-yl){3-[(3,5-dimethyl-1H-pyrazol-1-yl)carbon­yl]-5-methyl­indolizin-1-yl}methanone

There are two independent mol-ecules in the asymmetric unit of the title compound, C21H21N5O2. In each mol-ecule, the indolizine ring system is essentially planar, with r.m.s. deviations of 0.030 and 0.028 Å. The dihedral angles between the indolizine ring system and the pyrazole rings are 54.7 (3) and 8.6 (3)° in one mol-ecule and 54.4 (3) and 6.6 (3)° in the other. In the crystal, weak C-H⋯O ...

full text

4-(3,5-Dimethyl-1H-pyrazol-1-yl)benzene­sulfonamide

The two aromatic rings of the title compound, C(11)H(13)N(3)O(2)S, are inclined at an angle of 47.81 (4)°. The N atom of the amino unit is pyramidally coordinated; one H atom inter-acts with the sulfamyl O atom of an adjacent mol-ecule, forming a centrosymmetric hydrogen-bonded dimer. The dimers are linked by N-H⋯N hydrogen bonds, generating a three-dimensional network.

full text

My Resources

Save resource for easier access later

Save to my library Already added to my library

{@ msg_add @}


Journal title

volume 2  issue 2

pages  120- 126

publication date 2016-09-01

{@ msg @}

By following a journal you will be notified via email when a new issue of this journal is published.

Keywords

Hosted on Doprax cloud platform doprax.com

copyright © 2015-2023