97433-22-2Relevant academic research and scientific papers
Regioselective Radical Arene Amination for the Concise Synthesis ofortho-Phenylenediamines
Gillespie, James E.,Morrill, Charlotte,Phipps, Robert J.
, p. 9355 - 9360 (2021/07/19)
The formation of arene C-N bonds directly from C-H bonds is of great importance and there has been rapid recent development of methods for achieving this through radical mechanisms, often involving reactiveN-centered radicals. A major challenge associated with these advances is that of regiocontrol, with mixtures of regioisomeric products obtained in most protocols, limiting broader utility. We have designed a system that utilizes attractive noncovalent interactions between an anionic substrate and an incoming radical cation in order to guide the latter to the areneorthoposition. The anionic substrate takes the form of a sulfamate-protected aniline and telescoped cleavage of the sulfamate group after amination leads directly toortho-phenylenediamines, key building blocks for a range of medicinally relevant diazoles. Our method can deliver both free amines and monoalkyl amines allowing access to unsymmetrical, selectively monoalkylated benzimidazoles and benzotriazoles. As well as providing concise access to valuableortho-phenylenediamines, this work demonstrates the potential for utilizing noncovalent interactions to control positional selectivity in radical reactions.
Heterocyclic amines having central nervous system activity
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, (2008/06/13)
Tricyclic nitrogen containing compounds, having central nervous system activity of the following structural formula: STR1 and pharmaceutically acceptable salts thereof wherein R1, R2, and R3 are independently hydrogen, C1-6 alkyl, alkenyl, or alkynyl, C3-10 cycloalkyl, or R1 and R2 are joined to form a C3-7 cyclic amine which can contain additional heteroatoms; X is hydrogen, C1-6 alkyl halogen, hydroxy, alkoxy, cyano, carboxamide, carboxyl, or carboalkoxyl; A is SO2, N, CH, CH2, CHCH3, C=O, C=S, C-SCH3, C=NH, C-NH2, C-NHCH3, C--NHCOOCH3, or C--NHCN. B is CH2, CH, C=O, N, NH or N--CH3 ; n is 0 or 1; and D is CH, CH2, C=O, O, N, NH or N--CH3. These new compounds are suitable for treating schizophrenia, Parkinson's disease, anxiety, depression or as compounds for lowering blood pressure in animal or human hosts.
