A general synthetic route to prepare all four carboline regioisomers by photostimulated cyclization of anilinohalopyridines is described. The methodology affords various substituted carbolines in good excellent yields. In the case α-carbolines, SRN1 complements previously reported palladium-catalyzed approaches.

An efficient and simple protocol for the preparation of a series 9H-carbazoles by photostimulated SRN1 substitution reactions is presented. Substituted were synthesized in low to excellent yields (up 96%) through an intramolecular C–N bond formation 2′-halo[1,1′-biphenyl]-2-amines photoinitiated mechanism under mild "transition-metal-free" conditions. The biphenylamines used as substrates obtained with isolated ranging from 21% 84% two approaches: (A) cross-coupling Suzuki–Miyaura reaction...

Novel approaches for N- and O-desulfonylation under room temperature (rt) transition-metal-free conditions have been developed. The first methodology involves the transformation of a variety N-sulfonyl heterocycles phenyl benzenesulfonates to corresponding desulfonylated products in good excellent yields using only KOtBu dimethyl sulfoxide (DMSO) at rt. Alternately, visible light method has used deprotection N-methyl-N-arylsulfonamides with Hantzsch ester (HE) anion serving as...

A new and general synthetic route to prepare dibenzosultams is here reported. This approach involves the synthesis of N-aryl-2-halobenzenesulfonamides (3), followed by intramolecular C-C photoinduced arylation under soft conditions without use "Transition Metal". The photostimulated reactions exhibit very good tolerance different substituent groups with excellent isolated yields (42-98%) products. Moreover, it shown that LED (λ = 395 nm) an efficient light energy source initiate efficiently...

Abstract 3‐Substituted isoquinolin‐1‐(2 H )‐ones and fused have been obtained by the photostimulated S RN 1 reactions of 2‐iodobenzamide with enolates aromatic (acetophenone, 1‐(benzo[ d ][1,3]dioxol‐5‐yl)ethanone, 1‐ 2‐naphthyl methyl ketones, 2‐, 3‐, 4‐acetylpyridine), aliphatic (1‐adamantyl ketone), cyclic ketones (1‐ 2‐indanone, α‐ β‐tetralone, 1‐benzosuberone) in DMSO. (© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)

The photostimulated intramolecular ortho-arylation reactions of bromoarenes linked with pendant phenoxy containing N-substituted tetrahydroisoquinolines in liquid ammonia afforded aporphine (54-82% yield) alkaloid derivatives via SRN1 reactions. This strategy was extended for the first time to synthesis a homoaporphine derivative (40% yield). Tetrahydroisoquinoline precursors that contained electron-withdrawing groups on nitrogen (i.e., amides, sulfonamides, and carbamates) gave cyclized...

2-Substituted indoles (5a,b and 7) fused (9a-c, 11a,b, 12) have been obtained by the S(RN)1 mechanism from photostimulated reactions of o-iodoaniline (1) 1-halo-2-naphthalen-2-ylamines (3a,b) with enolate ions acyclic (acetophenone (6), 2- (4a) 4-acetylpyridine (4b)) cyclic ketones (1- (8a) 2-indanone (10a), 1- (8b) 2-tetralone (10b) 1-benzosuberone (8c)) in DMSO liquid ammonia as solvents. The carbanions derived 4a,b, 8a, 10b are novel nucleophiles that form new C-C bonds mechanism.

The synthesis of a series 6-substituted 2-pyrrolyl and 2-indolyl benzoxazoles by photostimulated C–O cyclization anions from 2-pyrrole carboxamides, 2-indole or 3-indole carboxamides has been found to proceed in good excellent yields (41–100%) DMSO liquid ammonia. pyrrole indole are obtained very isolated an amidation reaction different 2-haloanilines with 2-carboxylic acid 2- 3-carboxylic indole. To explain the regiochemical outcome these reactions (C–O arylation vs C–N C–C arylation),...

The reactivity of Pd-PVP NPs was evaluated in C–H bond activation for heterocycles synthesis under mild conditions. Their vitro activity against solid tumor cell lines assessed, revealing potential as anticancer agents.

A novel approach for the synthesis of tetracyclic indoles and 7-azaindoles is reported. The strategy involves four steps, with a fast rt intramolecular α-arylation ketones as key step. reaction was inspected synthetically to achieve 11 structures moderate very good yields (39–85%). Theoretical combined experimental studies led us propose probable polar mechanism (concerted SNAr).

Abstract BACKGROUND Growing concerns about sustainability have driven the search for eco‐friendly pest management solutions. Combining natural and synthetic compounds within controlled release systems is a promising strategy. This study investigated co‐encapsulation of compound citral (Cit) antifungal cyproconazole (CPZ) using two water‐based nanocarriers: solid lipid nanoparticles (SLNs) chitosan (CSNPs). RESULTS Both CSNPs SLNs loaded with Cit + CPZ displayed superior activity against...

Abstract We prepared a series of free NH and N ‐substituted dibenzonthiazines with potential anti‐tumor activity from ‐aryl‐benzenesulfonamides. A biological test synthesized compounds (59 samples) was performed in vitro measuring their antiproliferative against panel six human solid tumor cell lines its tubulin inhibitory activity. identified 6‐(phenylsulfonyl)‐6 H ‐dibenzo[ c , e ][1,2]thiazine 5,5‐dioxide 6‐tosyl‐6 as the best promising values (overall range 2–5.4 μM). Herein, we report...

Abstract magnified image The photostimulated reaction of enolate anions cyclic aromatic ketones such as substituted indan‐1‐ones and 3,4‐dihydro‐2 H ‐naphthalen‐1‐one with o ‐iodoaniline in DMSO affords 1‐, 2‐, 3‐, 4‐methoxy‐5,10‐dihydroindeno[1,2‐ b ]indoles (34‐40%), 1,2‐, 1,4‐, 2,3‐dimethoxy‐5,10‐dihydroindeno[1,2‐ ]‐indoles (31‐43%), 3‐methoxy‐5,11‐dihydro‐6 ‐benzo[ a ]carbazoles (42‐61%) by the S RN 1 mechanism one pot reactions.

Abstract This paper explores an original synthesis of novel heterocyclic compounds derived from photoinduced intramolecular coupling reactions, involving the formation C−N and C−C bonds. Specifically, two classes were targeted: 4 H ‐benzo[ e ]pyrazolo[1,5‐ b ][1,2,4]thiadiazines 5‐amino‐6‐thia‐4,5 a ‐diazaacephenanthrylenes. The synthetic strategy involved nucleophilic substitution reactions to prepare key sulfonamide starting substrates, followed by cyclization (via Substitution Radical...

Abstract A visible‐light‐driven approach towards phenanthridin‐6(5 H )‐one and carbazole rings synthesis under transition‐metal‐free conditions is here reported. Phenanthridinones carbazoles are synthesized through an intramolecular arylation of the corresponding N ‐(2‐halobenzyl)‐ ‐methylanilines or ‐substituted‐ ‐phenyl anilines using KO t Bu as base in dimethyl sulfoxide (DMSO) at room temperature (rt), employing blue light emitting diodes (LEDs) source. The reaction proceeds photo‐...

2-(Diphenylphosphino)benzoic acid, isolated as the ester, was obtained by photostimulated reaction of 2-chlorobenzoate ion with Ph 2 P -ions in good yield liquid ammonia.The did not occur dark; it inhibited m-dinitrobenzene and partially a radical trap such TEMPO.The results were consistent S RN 1 mechanism.No evidences for aromatic nucleophilic substitution (S N Ar) or benzyne mechanisms found.

Abstract The starting materials are generally prepared following the approaches shown for (IIIa) and (XIII).

Abstract It provides a convenient method to prepare all four carboline regioisomers in good high yields.

Abstract Optimized reaction conditions are established for an intramolecular S RN 1 type cyclization of 2‐(2‐haloarylamino)pyridines (I) to give pyrido[1,2‐a]benzimidazoles in good yield.

Abstract Irradiation of amides type (I), (IIII), and (V) allows a simple efficient access to pyrrolyl indolyl benzoxazoles.