27333-50-2

Usage

Uses

Used in Pharmaceutical Industry:
5-CHLORO-1,3-DIHYDRO-1,3,3-TRIMETHYLSPIRO[2 H-INDOLE-2,3'-[3 H]NAPHTH[2,1-B][1,4]OXAZINE] is used as a key intermediate in the synthesis of pharmaceutical products for its potential biological activities. Its unique structure and properties allow it to be a versatile building block in the development of new drugs with specific therapeutic effects.
Used in Agrochemical Industry:
In the agrochemical industry, 5-CHLORO-1,3-DIHYDRO-1,3,3-TRIMETHYLSPIRO[2 H-INDOLE-2,3'-[3 H]NAPHTH[2,1-B][1,4]OXAZINE] is utilized as a precursor in the production of agrochemicals, such as pesticides and herbicides. Its potential biological activities make it a valuable component in the development of effective and targeted agrochemical products.
Used in Research and Development:
5-CHLORO-1,3-DIHYDRO-1,3,3-TRIMETHYLSPIRO[2 H-INDOLE-2,3'-[3 H]NAPHTH[2,1-B][1,4]OXAZINE] is employed as a research compound in various scientific studies and experiments. Its unique structure and potential biological activities make it an interesting subject for exploring new chemical reactions, synthesis pathways, and applications in different fields.
Used in Drug Discovery:
As a heterocyclic organic molecule with potential biological activities, 5-CHLORO-1,3-DIHYDRO-1,3,3-TRIMETHYLSPIRO[2 H-INDOLE-2,3'-[3 H]NAPHTH[2,1-B][1,4]OXAZINE] is used in drug discovery processes to identify and develop new therapeutic agents. Its unique structure and properties can contribute to the design and synthesis of novel drugs with specific targets and mechanisms of action.
Used in Chemical Synthesis:
5-CHLORO-1,3-DIHYDRO-1,3,3-TRIMETHYLSPIRO[2 H-INDOLE-2,3'-[3 H]NAPHTH[2,1-B][1,4]OXAZINE] serves as a versatile building block in chemical synthesis, allowing for the creation of a wide range of compounds with diverse applications. Its unique spiro-structured indole and naphthoxazine ring system, along with the chlorine substituent, provide opportunities for further functionalization and modification, making it a valuable component in the synthesis of various organic compounds.

Upstream product

• 6872-17-9 5-chloro-1,3,3-trimethyl-2-methyleneindoline 
• 131-91-9 1-Nitroso-2-naphthol 
• 2834-92-6 1-amino-2-naphthol 

Downstream Products

• 7440-57-5 gold 

Relevant academic research and scientific papers

Spirobipyridopyrans, spirobinaphthopyrans, indolinospiropyridopyrans, indolinospironaphthopyrans and indolinospironaphtho-1,4-oxazines: Synthesis, study of X-ray crystal structure, antitumoral and antiviral evaluation

The novel racemic indolinospirobenzopyrans (5-7), indolinospironaphthopyrans (11-14) and indolinospironaphtho-1,4-oxazine (17) were synthesized by an aldol type of condensation of 1′,3′,3′- trimethyl-2 ′-methyleneindoline and its 5-substituted derivatives with an appropriately substituted hydroxybenzaldehyde, hydroxynaphthaldehyde or nitrosonaphthol. An unequivocal proof of the stereostructures of 9 and 17 was obtained by the single-crystal X-ray diffraction method. A substituted indoline ring and the benzopyran ring in 9 and the naphtho-1,4-oxazine moiety in 17 are interconnected via the common chiral atom and positioned almost perpendicularly to each other. The five-membered 2,3-dihydropyrrolo moiety of the indoline ring adopts an envelope conformation in both structures. Of all the compounds of this series, spirobipyridopyran (1) inhibited specifically the growth of human melanoma (HBL) (IC50: 0.9 μM) cells but not the growth of normal fibroblasts (WI38). Indolinospirobenzopyrans (8-10) showed significant cytostatic activities against all tumor cell lines. However, these compounds also exhibited a cytotoxic effect on normal human fibroblasts. The indolinospirobenzopyrans 4, 6-8, 10 and the indolinospironaphtho-1,4-oxazine 16 showed, albeit modest, selectivity as antiviral agents against varicella-zoster virus (VZV) and/or cytomegalovirus (CMV) (EC50 within the concentration range of 1.0-12.6 μM).

Microwave-Assisted Solvent-Free Synthesis of the Substituted Spiroindolinonaphth[2,1-b][1,4]oxazines

The synthesis of the substituted spiroindolinonaphth[2,1-b][1,4]oxazines 3a-e is developed through the condensation of 2-methylene-1,3,3-trimethylindoline derivatives and 1-nitroso-2-naphthol under microwave irradiation. In the same conditions, in presence of morpholine the 6′-morpholinosubstituted compounds 4a, b, d, e are formed. The main advantages of the method are the short reaction time, solvent-free reaction condition, cleaner reaction products and the higher product yields in comparison with known methods of synthesis.

NMR studies of the structure of the photoinduced forms of photochromic spironaphthoxazines

Irradiation at 355 nm with a pulsed laser of the colourless 1,3-dihydro-1,3,3-trimethylspiro[2H-indole-2,3′-[3H]-naphth[2,1-b][1,4] oxazine] results in formation of photomerocyanines (coloured forms of photochromic compounds); this and its chloro derivative were studied by NMR spectroscopy. This has allowed us to confirm the structure of the stereoisomers. The colourless and coloured forms exist in thermal equilibrium. Integration of certain photomerocyanine signals allowed us to calculate the thermal kinetics of bleaching k, the half-life τ and the activation enthalpy ΔH? at different low temperatures and from these temperature dependence studies of the thermal decay rate, the thermal energy barrier for the decay of the coloured metastable state to the colourless form was determined.

Synthesis of photochromic spirooxazines from 1-amino-2-naphthols

A synthetic access to photochromic spirooxazines is developed through the condensation of methylene-substituted azaheterocycles on 1-amino-2- naphthols in presence of an oxidizing agent. Compared to usual preparation of this kind of compounds (via 1-nitroso-2-naphthols), yields are generally good and approaches to further spiroheterocyclic oxazines are possible.

SYNTHESE DE QUELQUES SPIRO ET SPIRO PHOTOCHROMIQUES. APPLICATION DE LA METHODOLOGIE DE LA RECHERCHE EXPERIMENTALE

Some spiro I and spiro II substituted by different groups were synthesized in order to evaluate their photochromic properties and to optimize the preparation of spiroheterocyclic systems.In addition, some spiro III were also prepared as reference compounds.Their physical and spectroscopic characteristics (UV, 1H and 13C) were determined.A study using the experimental design methodology allowed to point out the most important factors for improving the reaction yields. KEYWORDS: Photochromism, spirooxazines, spiropyrans, synthesis, 1H NMR, experimental design methodology.

Sensibilisation du photochromisme de spirooxazines par transfert d'energie triplet-triplet

The present publication describes sensitized photocoloration by triplet-triplet energy transfer of some photochromic spirooxazines.The dominant reaction leading to the colored dye product B in the direct photolysis of the spirooxazine (SPO) in toluene involves the singlet excited state but the results obtained in this work show that both triplet and singlet states are involved in the color-forming reaction.We employed sensitizers of decreasing triplet energy in an attempt to locate the triplet level in the SPO.From the triplet energies of the sensitizers of the SPO color formation it can be concluded that the energy of the spirooxazine triplet state is about 212 kJ.mol-1.The camphorquinone (CQ) sensitizes the formation of B.This compound is particularly suitable for investigation of sensitized photocoloration of spirooxazines since it absorbs in a region of the spectrum where SPO does not absorb (λmax = 471 nm).Then, it is possible to extend the photochromic properties of the SPO to the visible region (λ 500 nm) for industrial applications.The absorption spectra of the colored form were determined for the direct and sensitized photolysis in toluene solutions.

The pH Control of the Decolouration Rate of Spironaphthoxazine Derivatives

The thermal stablility of the coloured open form of 5-methoxy- (7) and 5'-piperidinomethyl-1,3,3-trimethylspiro(indoline-2,3'-naphthooxazine) (6) is strongly dependent on pH.

Photochromic lens

A photochromic lens is composed of a lens member made of a lens resin; and a photochromic layer applied on at least one side of the lens member and formed of a resin of a three-dimensional network structure. The layer-forming resin contains a spirooxazine compound represented by the following general formula (I): STR1 wherein R1 means a hydrogen or halogen atom or a cyano, C1-6 alkyl or C1-6 alkoxy group, and R2 denotes a C1-6 alkyl group, --CH2)n COOH, --CH2)n CN, substituted arylalkyl group or --CH2)n COOR in which R is a C1-6 alkyl group and n stands for an integer of 1-4. The layer-forming resin may additionally contain a phenol resin and/or a phenolic compound. A hard coat layer may optionally be applied on the surface of the photochromic layer.