Carbazole Ring System Research Articles

3,6-Dibromo-9-(4-tolylsulfonyl)-9H-carbazole

The title compound, C19H13Br2NO2S, was synthesized by N-alkylation of 4-methylbenzenesulfonyl chloride with 3,6-dibromo-9H-carbazole. The carbazole ring system is essentially planar, with a mean deviation of 0.024 Å, and makes a dihedral angle of 75.46 (9)° with the plane of the benzene ring.

9-[4-(6-Bromo-4-phenylnaphthalen-2-yl)phenyl]-9H-carbazole

The title compound, C34H22BrN, was synthesized by N-alkylation of 7-bromo-3-(4-bromophenyl)-1-phenylnaphthalene with 9H-carbazole. The carbazole ring system is essentially planar and makes a dihedral angle of 48.63 (9)° with the plane of the adjacent benzene ring.

9-(p-Tolylsulfonyl)-9H-carbazole

Two independent molecules constitute the asymmetric unit of the title compound, C19H15NO2S, which was synthesized by N-alkylation of 4-methylbenzenesulfonyl chloride with carbazole. The carbazole ring system is essentially planar and forms a dihedral angle with the benzene ring of 85.1 (7)° [83.9 (7)° for the second molecule]. In the crystal structure, weak C—H...O interactions are observed.

Bis(9-ethylcarbazol-3-yl)ethane

In the title compound, C30H28N2, each carbazole skeleton is essentially planar. The planes of the two carbazole ring systems are nearly parallel, with a dihedral angle of 2.33 (19)°. The crystal packing is stabilized only by van der Waals forces and weak C—H...π interactions.

9,9′-Diethyl-3,3′-di-9H-carbazolyl

In the title compound, C28H24N2, the carbazole ring systems are essentially planar to within 0.076 (3) Å. The dihedral angle between the planes of the ring systems is 40.38 (4)°. The contribution of inter­molecular π–π inter­actions to the mol­ecular stacking is observed.

3,6-Dibromo-9-(4-pyridylmethyl)-9H-carbazole

The title compound, C18H12Br2N2, was synthesized by N-alkyl­ation of 4-chloro­methyl­pyridine with 3,6-dibromo-9H-carbazole. The carbazole ring system is essentially planar, with a mean deviation of 0.012 Å, and makes a dihedral angle of 83.2 (8)° with the plane of the pyridine ring. In the crystal structure, weak C—H⋯Br inter­actions are observed.

(3,6-Dibromo-9H-carbazol-9-yl)(phenyl)methanone

The title compound, C19H11Br2NO, was synthesized by N-alkyl­ation of benzoyl chloride with 3,6-dibromo-9H-carbazole. The carbazole ring system is essentially planar and makes a dihedral angle of 62.2 (1)° with the plane of the benzene ring. Weak C—H⋯Br hydrogen bonding occurs in the crystal structure.

9-(4-Chlorobenzyl)-9H-carbazole

The title compound, C19H14ClN, was synthesized by N-alkyl­ation of carbazole with 1-chloro-4-(chloro­meth­yl)benzene. The carbazole ring system is essentially planar and makes a dihedral angle of 109.6 (5)° with the plane of the benzene ring.

9-Allyl-3,6-dibromo-9H-carbazole

The title compound, C15H11Br2N, was synthesized by N-alkyl­ation of 3-bromo­propene with 3,6-dibromo-9H-carbazole. The carbazole ring system is essentially planar and perpendicular to the pendant allyl substituent.

3,6-Dibromo-9-(4-chlorobenzyl)-9H-carbazole

The title compound, C19H12Br2ClN, was synthesized by N-alkyl­ation of 1-chloro-4-(chloro­meth­yl)benzene with 3,6-dibromo-9H-carbazole. The carbazole ring system is essentially planar, with a mean deviation of 0.026 Å, and makes a dihedral angle of 75.16 (7)° with the plane of the benzene ring.

3,6-Dibromo-9-(3-pyridylmethyl)-9H-carbazole

The title compound, C18H12Br2N2, was synthesized by N-alkyl­ation of 3-(chloro­meth­yl)pyridine with 3,6-dibromo-9H-carbazole. The carbazole ring system is essentially planar, with a mean deviation of 0.0138 Å, and forms a dihedral angle of 96.7 (8)° with the plane of the pyridine ring. In the crystal structure, π–π inter­actions and weak C—H⋯Br inter­actions are observed.

9-(4-Methylbenzyl)-9H-carbazole

The title compound, C20H17N, was synthesized by N-alkyl­ation of 1-chloro­methyl-4-methyl­benzene with carbazole. The carbazole ring system is essentially planar, with a mean deviation of 0.029 Å, and makes a dihedral angle of 109 (5)° with the plane of the benzene ring.

3,6-Dibromo-9-isopropyl-9H-carbazole

The title compound, C15H13Br2N, was synthesized by N-alkyl­ation of 2-bromo­propane with 3,6-dibromo-9H-carb­azole. The carbazole ring system is essentially planar, with a mean deviation of 0.01 Å. The isopropyl group is disordered over two positions across a pseudo-mirror plane perpendicular to the carbazole ring system.

9-(2-Pyridylmethyl)carbazole

In the title compound, C18H14N2, the carbazole and pyridine ring systems are each essentially planar. The asymmetric unit contains three independent mol­ecules. The mol­ecular structure is stabilized by an inter­molecular C—H⋯N hydrogen bond.

3,6-Dibromo-9-hexyl-9H-carbazole

The title compound, C18H19Br2N, was synthesized by N-alkyl­ation of 1-bromo­hexane with 3,6-dibromo-9H-carbazole. The carbazole ring system is essentially planar and the n-hexyl chain is in the fully extended conformation.

A New Total Synthesis of an Indolo[3,2‐j]phenanthridine Alkaloid Calothrixin B.

AbstractFor Abstract see ChemInform Abstract in Full Text.

9-Benzyl-3,6-dibromo-9H-carbazole

Two independent mol­ecules comprise the asymmetric unit of the title compound, C19H13Br2N, which was synthesized by N-alkyl­ation of benzyl bromide with 3,6-dibromo-9H-carbazole. The carbazole ring system is essentially planar and forms a dihedral angle with the pendant phenyl ring of 66.0 (2)° [70.6 (2)° for the second mol­ecule]. In the crystal structure, π–π inter­actions and weak C—H⋯Br inter­actions are observed.

9-(4-Nitrophenyl)-9H-carbazole

In the title compound, C18H12N2O2, the carbazole ring system is essentially planar and makes a dihedral angle of 53.08 (4)° with the plane of the nitro­benzene ring. In the crystal structure, inversion-related mol­ecules form a C—H⋯O hydrogen-bonded dimer.

3,6-Dibromo-9-ethyl-9H-carbazole

The title compound, C14H11Br2N, was synthesized by N-alkyl­ation of bromo­ethane with 3,6-dibromo-9H-carbazole. The carbazole ring system is essentially planar and makes a dihedral angle of 94.7 (3)° with the plane formed by the eth­yl C and carbazole N atoms.

A new total synthesis of an indolo[3,2- j]phenanthridine alkaloid calothrixin B

A new total synthesis of calothrixin B is described. The key step is an allene-mediated electrocyclic reaction involving the indole 2,3-bond for the construction of a suitable 4-oxygenated 2,3,4-trisubstituted carbazole ring system.