Related Experiment Video
Updated: Jun 1, 2026
![Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions](/_next/image?url=https%3A%2F%2Fcloudfront.jove.com%2FCDNSource%2Fteasers%2F60786.jpg&w=3840&q=50)
Cercosporin-Photocatalyzed [4+1]- and [4+2]-Annulations of Azoalkenes Under Mild Conditions
Published on: July 17, 2020
7-(4-Methoxy-phen-yl)-5-methyl-9-phenyl-7H-pyrrolo[2',3':4,5]pyrimido[1,6-d]tetrazole
Abstract:
The title compound, C(20)H(16)N(6)O, is composed of a tetra-zolo ring and a 4-methoxy-phenyl and a benzene-substituted pyrrole ring at the 7 and 9 positions fused to a pyrimidine ring in a nearly planar fashion [maximum deviation of 0.018 (1) Å for the fused ring system]. A methyl group at the 5 position is also in the plane of the hetero cyclic system. The dihedral angle between the mean planes of the benzene and 4-methoxy-phenyl rings is 40.4 (2)°. The dihedral angles between the mean planes of the pyrimidine and the benzene and 4-methoxy-phenyl rings are 15.6 (5)° and 52.6 (7)°, respectively. A weak intra-molecular C-H⋯N hydrogen bond inter-action, which forms an S(7) graph-set motif, helps to establish the relative conformations of the tetrazolo and benzene rings. In the crystal, weak inter-molecular C-H⋯O, C-H⋯π and π-π stacking inter-actions [centroid-centroid distances = 3.5270 (16), 3.5113 (16), 3.7275 (17) and 3.7866 (17) Å] link the mol-ecules into a two-dimensional array obliquely parallel to (101) and propagating along the b axis.
Related Concept Videos
Five-Membered Heterocyclic Aromatic Compounds: Overview
Aromatic Hydrocarbon Cations: Structural Overview
Removing one hydrogen from the intervening CH2 group with both...
Basicity of Heterocyclic Aromatic Amines

