66073-33-4

Usage

Synthesis Reference(s)

Journal of Heterocyclic Chemistry, 26, p. 71, 1989 DOI: 10.1002/jhet.5570260114

InChI:InChI=1/C12H13NO5/c1-2-18-12(15)8-10(14)7-9-5-3-4-6-11(9)13(16)17/h3-6H,2,7-8H2,1H3

Upstream product

• 3740-52-1 2-(2-nitrophenyl)acetic acid 
• 6148-64-7 ethyl potassium malonate 
• 64-17-5 ethanol 
• 1069111-98-3 5-[1-hydroxy-2-(2-nitrophenyl)ethylidene]-2,2-dimethyl-1,3-dioxane-4,6-dione 
• 22751-23-1 (2-nitrophenyl)acetyl chloride 
• 119209-55-1 propanedioic acid monoethyl ester dilithium salt 
• 61417-33-2 ethyl 2-acetyl-3-oxo-4-(2-nitrophenyl)butanoate 

Downstream Products

• 33588-64-6 ethyl 2-(1H-indol-2-yl)acetate 
• 99185-25-8 4-(2-nitro-phenyl)-acetoacetic acid 

Relevant academic research and scientific papers

Exploring of indole derivatives for ESIPT emission: A new ESIPT-based fluorescence skeleton and TD-DFT calculations

Appropriate synthesis methods gave six different indole derivatives substituted at the C-2 or C-3 position. ESIPT emission capacities of these derivatives were investigated. It was concluded that the indole derivative containing the 1,2-dicarbonyl group at the C-2 position has ESIPT emission. Although adding water to the DMSO solution of the ESIPT-based molecule (9:1) resulted in ESIPT quenching, steady-state measurements in MeOH did not occur ESIPT quenching. TD-DFT calculation for uncovering the ESIPT mechanism emerged that the ESIPT mechanism occurred as a barrierless process. The X-ray analysis and DFT conformational analysis revealed that NH and CO groups involving proton transfer mechanisms are in the cis position. A mono-exponential decay was observed in DMSO and MeOH solutions, in which lifetimes were measured as 6.1 and 5.5 ns, respectively. pH studies revealed that acidic and basic solutions of molecule 7 did not influence ESIPT emission.

Environmentally Friendly Synthesis of Indoline Derivatives using Flow-Chemistry Techniques

Flow chemistry proved to be a valuable technique to improve the synthesis route to melanin-concentrating hormone receptor 1 (MCHr1) antagonists with the 1H,2H,3H,4H,5H-[1,4]diazepino[1,7-a]indole scaffold. A one-step route for the heterogeneous catalytic hydrogenation of ethyl 4-(2-nitrophenyl)-3-oxobutanoate for the synthesis of ethyl 2-(2,3-dihydro-1H-indol-2-yl)acetate was developed, and the use of common reducing chemicals was avoided. N-Alkylation of the indoline nitrogen atom was also optimized by using a purpose-built flow reactor and by design of experiment (DoE). Applying an optimal set of parameters allowed us to decrease the amount of carcinogenic 1,2-dibromoethane used by a factor of 10. Additionally, nearly complete conversion was achieved in a fraction of the original reaction time (30 min vs. 4 d); therefore, the productivity (space-time yield) of the flow-reactor system was proven to be ca. 200 times higher than that of the batch process.

Diastereodivergence and appendage diversity in the multicomponent synthesis of aryl-pyrrolo-tetrahydrocarbazoles

A one-pot approach using a subsequent Cu(II)/Cu(I) catalysis and a highly diastereodivergent three-component reaction allow an easy access to various aryl-pyrrolo-tetrahydrocarbazoles with the control of up to four variable fragments and two different diastereoselectivities.

Synthesis, NMR conformational analysis and pharmacological evaluation of 7,7a,13,14-tetrahydro-6H-cyclobuta[b]pyrimido[1,2-a:3,4-a′]diindole analogues as melatonin receptor ligands

A structure for the self-condensation product of 2-(1H-indol-2-yl)ethyl tosylate 2a, previously proposed as 6,7,14,15-tetrahydro-15aH-azocino[1,2-a:6,5- b]diindole 3a, was revised based on the 13C-2D-INADEQUATE experiment, and proved to be 7,7a,13,14-tetrahydro-6H-cyclobuta[b]pyrimido[1,2-a:3,4- a′]diindole 4a. A mechanism for the unexpected formation of this novel hexacyclic heterocycle was proposed and its NMR solution structure was elucidated. Five derivatives of the title ring skeleton 12-16 designed as melatonin receptor ligands were synthesized and their affinities for the human MT1 and MT2 receptors were determined. Both butyramides 13 and 15, as well as the non-methoxy acetamide 12 exhibited micromolar binding affinities for both receptors being slightly MT2 selective. The methoxy acetamide 14 showed the best pharmacological profile exhibiting a five times higher affinity for MT1 (Ki = 49 nM) than for MT2 (Ki = 246 nM) receptor. This journal is The Royal Society of Chemistry.

PYRAZOLO[3,4-c]QUINOLINES, PYRAZOLO[3,4-c]NAPHTHYRIDINES, ANALOGS THEREOF, AND METHODS

Pyrazolo[3,4-c]quinolines, pyrazolo[4,5-c]naphthyridines, and analogs thereof, eg., 6,7,8,9-tetrahydro pyrazolo[3,4-c]quinolines, and, pharmaceutical compositions containing the compounds, intermediates, methods of making these compounds, and methods of use of these compounds as immunomodulators, for inhibiting cytokine biosynthesis in animals and in the therapeutic or prophylactic treatment of diseases by inhibiting cytokine biosynthesis are disclosed.

Diels-Alder Reactivity of Pyranoindol-3-ones, Indole 2,3-Quinodimethane Analogues

The pyranoindol-3-ones (7) are stable indole-2,3-quinodimethane type dienes, which undergo Diels-Alder reaction with alkynes to give, after loss of carbon dioxide, carbazoles.The reactivity of the diene is increased by the presence of the electron-withdrawing t-butoxycarbonyl group on the indole nitrogen.The pyranoindolones (7) are less reactive, and exhibit the opposite regiochemistry in their Diels-Alder reactions than the isomeric pyranoindol-3-ones (1).Factors which affect the regiochemistry of the Diels-Alder reaction are discussed.

Synthesis and Reactions of 6,11-Dihydro-5H-pyrido-benzazepin-5-one

A three-step synthesis for the new 6,11-dihydro-5H-pyridobenzazepinone (6a) and its derivatives 6b-d is reported.The reactivity of the tricyclic ring system is outlined by preparing the derivatives 7-15 from the parent compound 6a.The products a

Tricyclic heteroaromatic systems. 1,2,3,4-Tetrahydropyrazolo[4,3-c][1]benzazepin-1-ones as potential antitumor agents

The synthesis of 1,2,3,4-tetrahydropyrazolo[4,3-c][1]benzazepin-1-ones and that of its 10-methyl derivative is reported. The preparation of the latter from 3-(2-aminobenzyl)-3-pyrazolin-5-one and triethyl orthoformate gave as the main product a derivative

1-Nitroso-1,2,3,4-tetrahydroquinoline and 1-nitroso-indoline compounds

This invention relates to N-nitroso compounds having the formula STR1 wherein R and R' each are selected from hydrogen and alkyl, Z is --CN or --COOR" wherein R" is alkyl and n is a positive integer from 1 to 7. These compounds are useful as intermediates in the preparation of photographic silver halide developing agents.