50374-92-0

Usage

InChI:InChI=1/C13H14N2/c1-15(11-7-3-2-4-8-11)13-10-6-5-9-12(13)14/h2-10H,14H2,1H3

Upstream product

• 52997-62-3 2-nitro-N-methyl-N-phenylaniline 
• 100-61-8 N-methylaniline 
• 17763-67-6 Phenyl triflate 
• 108-86-1 bromobenzene 
• 88-73-3 2-Chloronitrobenzene 
• 88-74-4 2-nitro-aniline 
• 119-75-5 2-nitro-N-phenylaniline 
• 62-53-3 aniline 

Downstream Products

• 1484-12-4 N-methylcarbazole 
• 1429049-04-6 N¹-methyl-N²-(2-nitrophenyl)-N¹-phenylbenzene-1,2-diamine 
• 1429049-14-8 N¹-(2-aminophenyl)-N¹-butyl-N²-methyl-N²-phenylbenzene-1,2-diamine 
• 1429049-11-5 N¹-(2-aminophenyl)-N¹,N²-dimethyl-N²-phenylbenzene-1,2-diamine 
• 1429049-18-2 N¹-(2-(butylamino)phenyl)-N²-methyl-N²-phenylbenzene-1,2-diamine  
• 1429049-17-1 N¹-methyl-N²-(2-(methylamino)phenyl)-N¹-phenylbenzene-1,2-diamine  
• 1429049-09-1 N¹-butyl-N²-methyl-N¹-(2-nitrophenyl)-N²-phenylbenzene-1,2-diamine 
• 1429049-06-8 N¹,N²-dimethyl-N¹-(2-nitrophenyl)-N²-phenylbenzene-1,2-diamine  
• 2622-63-1 1-methyl-2-phenylbenzimidazole 
• 2219-12-7 2-(1-methyl-1H-benzo[d]imidazol-2-yl)phenol 
• 94212-05-2 2-(1-phenyl-1H-benzo[d]imidazole-2-yl)phenol 
• 1354644-36-2 N-(2-allyloxybenzylidene)-N'-methyl-N'-phenylbenzene-1,2-diamine 
• 92245-11-9 N-Methyl-o-formamido-diphenylamin 
• 2622-67-5 1,2-diphenyl-1H-benzoimidazole 

Relevant academic research and scientific papers

1,2-Difunctionalization of Aryl Triflates: A Direct and Modular Access to Diversely Functionalized Anilines

ortho-Amino difunctionalization of aryl triflates has been achieved via a three-component reaction. The cascade reaction proceeds through a zincate base-mediated deprotonative formation of a reactive aryne intermediate, in situ nucleophilic addition, and coupling with electrophilic partners. This strategy leverages the advantageous reactivity of organozincate intermediates, enabling the installation of various functionalities such as amine, azide, oxygen, sulfur, halide, alkynyl, aryl, vinyl, and alkyl groups in a modular manner for the synthesis of diverse aniline skeletons.

Apparent alkyl transfer and phenazine formation via an aryne intermediate

Treatment of chlorotriaryl derivatives 3a and 3d or fluorotriaryl derivatives 3b and 3e with potassium diisopropylamide afforded alkyl-shifted phenazine derivatives 5a/5b, rather than the expected 9-membered triazaorthocyclophane 2a. The phenazine derivatives were isolated in 78-98% yield depending on the halogen and alkyl group present. In the absence of the halogen (chloro or fluoro), the apparent alkyl shift proceeds more slowly and cannot proceed via the intermediacy of the aryne intermediate. Mechanistic possibilities include intramolecular nucleophilic attack on an aryne intermediate leading to a zwitterionic intermediate and alkyl transfer via a 5-endo-tet process, or via a Smiles rearrangement.

NON STEROIDAL GLUCOCORTICOID RECEPTOR MODULATORS

The present invention relates to compounds having general Formula (I) or a pharmaceutically acceptable salt thereof. In this formula R1 is H or (1-4C)alkyl; R2 is -C(O)R15 or -S(O)2R15; R3 is H, (1-4C)alkyl or -OR16; R4 is H, (1-4C)alkyl or -OR16; R6 is H or -C(H)NOR16; R7 is H or halogen, cyano; (1-6C)alkyl, (2-6C)alkenyl or (2- 6C)alkynyl, all three optionally substituted with OH, halogen or NH2 ;-C(H)NOR16, - OR16, -C(O)R16, or -C(O)OR16; R8 is H, cyano, halogen, nitro; (1-6C) alkyl, (2- 6C)alkenyl, (2-6C)alkynyl or -O(1-6C)alkyl, all optionally substituted with amino, hydroxyl or halogen; (hetero)aryl, optionally substituted with cyano, halogen, (1- 4C)alkyl, (1-4C)alkoxy, (1-4C)alkoxy(1-4C)alkyl; -C(O)R18, -C(O)OR19, -C(O)NHR17, -NHC(O)R20, -C(1-4C)alkylNOR21; -C(H)NOR16, or -NHS(O)2R21; R9 is H, halogen, cyano or (1-4C)alkyl optionally substituted with halogen; R10is H or (1-4C)alkyl; R11 is H; R12 is H, cyano or (1-4C)alkyl; R13 is H, (1-4C)alkyl, halogen or formyl; R14 is H, halogen, cyano, (1-4C)alkyl, (2-6C)alkenyl, C(O)R21 or (hetero)aryl; R15 is H; (1- 6C)alkyl, (2-6C)alkenyl, (2-6C)alkynyl,-O(2-6C)alkyl, -O(2-6C)alkenyl or -O(2- 6C)alkynyl, all optionally substituted with one or more OH, halogen, cyano or (hetero)aryl, (hetero)aryl, optionally substituted with (1-4C)alkyl, halogen, cyano, nitro or amino, NH2, (di)(1-4C)alkylamino, (1-4C)alkyl(1-4C)alkoxyamine, (1- 4C)alkylt hio(1-4C)alkyl or (1-4C)alkoxy(1-4C)alkyl; R16 is H, (1-6C)alkyl, (2- 6C)alkenyl or (2-6C)alkynyl; R17 is H, (1-6C)alkyl, optionally substituted with halogen, (1-4C)alkoxy or (hetero)aryl, optionally substituted with halogen, (1-4C)alkyl or (1- 25 4C)alkoxy; (3-6C)cycloalkyl or (hetero)aryl, optio nally substituted with halogen, (1- 4C)alkyl or (1-4C)alkoxy; R18 is H, NH2, C(O)R21 or (1-4C)alkyl, optionally substituted with OH, halogen, cyano or -S(1-4C)alkyl; R19 is H or (1-6C)alkyl, optionally substituted with OH or halogen; R20 is H, (1-6C)alkyl or (2-6C)alkenyl, both optionally substituted by halogen, O(1-6C)alkyl, (hetero)aryl, optionally substituted with (1- 4C)alkyl or halogen; (3-6C)cycloalkyl; (1-6C)alkoxy; (1-6C)alkenyloxy; or (hetero)aryl, optionally subst ituted with (1-4C)alkyl); NH2, -NH(1-6C)alkyl or -NH(hetero)aryl and R21 is H or (1-6C)alkyl. The present invention also relates to pharmaceutical compositions comprising said compounds and the use of these derivatives to modulate glucocorticoid receptor activity.

11-(Tetrahydro-3 and 4-pyridinyl)dibenzo[b,e][1,4]diazepines undergo novel rearrangements on treatment with concentrated HBr

11-(1,2,5,6-Tetrahydro-1-methyl-3-pyridinyl)-5-methyl-5H-dibenzo[b,e][1,4] diazepine on heating in conc. HBr afforded trans-5-(2-aminophenyl)-1,3,4,4a,5,10a-hexahydro-2-methylbenzo[b][1,6] naphthyridin-10(2H)-one in one step. The isomer 11-(1,2,5,6-tetrahydro-1-methyl-4-pyridinyl)-5-methyl-5H-dibenzo[b,e][1,4] diazepine underwent a novel rearrangement resulting in the pentacycle, 4-amino-5,13-diaza-13-methyl-bicyclo[3.3.1]nonan[6,7,8-k,l]acridine.

Regulation of retinoidal actions by diazepinylbenzoic acids. Retinoid synergists which activate the RXR-RAR heterodimers

In human HL-60 promyelocytic leukemia cells, diazepinylbenzoic acid derivatives can exhibit either antagonistic or synergistic effects on the differentiation-inducing activities of natural or synthetic retinoids, the activity depending largely on the nature of the substituents on the diazepine ring. Thus, a benzolog of the retinoid antagonist LE135 (6), 4-(13H- 10,11,12,13-tetrahydro-10,10,13,13,15-pentamethyldinaphtho[2,3-b][1,2- e]diazepin-7-yl)benzoic acid (LE540, 17), exhibits a 1 order of magnitude higher antagonistic potential than the parental LE135 (6). In contrast, 4- [5H-2,3-(2,5-dimethyl-2,5-hexano)-5-methyldibenzo[b,e][1,4]diazepin-11-yl]- benzoic acid (HX600, 7), a structural isomer of the antagonistic LE135 (6), enhanced HL-60 cell differentiation induced by RAR agonists, such as Am80 (2). This synergistic effect was further increased for a thiazepine, HX630 (29), and an azepine derivative, HX640 (30); both synergized with Am80 (2) more potently than HX600 (7). Notably, the negative and positive effects of the azepine derivatives on retinoidal actions can be related to their RAR- antagonistic and RXR-agonistic properties, respectively, in the context of the RAR-RXR heterodimer.