27300-29-4

Usage

Uses

Used in Pharmaceutical Industry:
3,11-Dihydro-3,3-dimethylpyrano[3,2-a]carbazole-5-carbaldehyde is used as a pharmaceutical compound for its potential therapeutic applications. The compound's unique structure and properties make it a promising candidate for the development of new drugs, particularly in the areas of cancer treatment and other diseases.
Used in Chemical Research:
In the field of chemical research, 3,11-Dihydro-3,3-dimethylpyrano[3,2-a]carbazole-5-carbaldehyde serves as a valuable compound for studying the properties and reactivity of carbazole alkaloids. Its unique structure and absorption characteristics can provide insights into the behavior of similar compounds and contribute to the advancement of chemical knowledge.
Used in Material Science:
3,11-Dihydro-3,3-dimethylpyrano[3,2-a]carbazole-5-carbaldehyde may also find applications in material science, particularly in the development of new materials with specific optical, electronic, or structural properties. The compound's unique structure and absorption characteristics could be exploited to create novel materials with tailored properties for various applications.

References

Chakraborty, Das., Chern. Cornrnun., 967 (1966)Revised structure: Joshi, Kamat, Gawad., Tetrahedron, 26, 1475 (1970)

Upstream product

• 27300-31-8 murrastinine-B 
• 23095-44-5 girinimbine 
• 5428-54-6 2-methyl-5-nitrophenol 
• 184896-30-8 5-amino-2,2,8-trimethylchromene 
• 184896-36-4 2,2,8-trimethyl-5-nitro-2H-chromene 
• 184896-34-2 1-methyl-2-[(2-methylbut-3-yn-2-yl)oxy]-4-nitrobenzene 
• 99-55-8 2-methyl-5-nitroaniline 
• 40463-86-3 5-hydroxymethyl-3,3-dimethyl-1-(toluene-4-sulfonyloxy)-1,2,3,11-tetrahydro-pyrano[3,2-a]carbazole 
• 219492-11-2 2-(benzyloxy)-1-methyl-4-nitrobenzene 
• 219492-12-3 3-(benzyloxy)-4-methylaniline 
• 13120-77-9 2-methyl-5-nitroanisole 
• 16452-01-0 ortho-cresidine 
• 24224-30-4 2-hydroxy-3-methyl-9H-carbazole 
• 19021-53-5 methyl (2-methylbut-3-yn-2-yl)carbonate 

Relevant academic research and scientific papers

Pd-Catalyzed Formal [3 + 3] Heteroannulation of Allylic gem-Diacetates: Synthesis of Chromene-Based Natural Products and Exploration of Photochromic Properties

Palladium-catalyzed allylic alkylation reactions of allylic gem-diacetates are rarely explored. This work unveils an unusual chemical reactivity pattern of allylic gem-diacetates and establishes them as new prototypes to synthesize complex benzo[f]chromene systems. Under the reaction conditions, the diacetates behave as 1,3-dicationic equivalents and undergo a [3 + 3] heteroannulation with 2-naphthols (and meta-substituted phenols) to produce novel polycyclic chromenes possessing spiro-, tri-, and tetrasubstituted carbon centers. The versatility of the method is demonstrated in the synthesis of several chromene-based bioactive natural products. Further, interesting photochromic properties of the new classes of benzo[f]chromenes are also discovered.

Pyrano[3,2-a]carbazole alkaloids as effective agents against ischemic stroke in vitro and in vivo

A series of pyrano[3,2-a]carbazole alkaloids were designed and synthesized as analogues of Claulansine F (Clau F, 10a) isolated from Clausena lansium. Some of compounds showed strong neuroprotective effects and were promising agents against ischemic stroke. Among these compounds, 7c was the most active in inhibiting the programmed death of PC12 cells and primary cortical neurons. This compound induced neuroprotection following ischemic reperfusion and decreased neurological deficit scores in treated animals. Furthermore, 7c could penetrate the blood-brain barrier (BBB) in rats, and its exposure in the brain was 4.3-fold higher than that in plasma. More importantly, compared to edaravone, 7c exhibited stronger free radical scavenging activity. Our findings suggest that 7c may be promising for further evaluation as an intervention for ischemic stroke.

Divergent and Orthogonal Approach to Carbazoles and Pyridoindoles from Oxindoles via Indole Intermediates

The previously unexplored Grignard addition to oxindoles provides a regiospecific approach to 2- and 2,3-disubstituted indole derivatives in high yields via a one-pot aromatization driven dehydration pathway. This method allows a convenient preparation of diallyl indoles that are used as ring-closing metathesis (RCM) precursors for the orthogonal synthesis of pyrido[1,2-a]indoles and carbazoles. The synthetic utility of this method is illustrated by the synthesis of a microtubulin inhibitor and naturally occurring carbazole alkaloids.

"on Water" Promoted Ullmann-Type C-N Bond-Forming Reactions: Application to Carbazole Alkaloids by Selective N-Arylation of Aminophenols

The Ullmann-type cross coupling of a variety of aromatic, aliphatic amines with aryl halides is reported using a CuI-based catalytic system in combination with an easily accessible prolinamide ligand in aqueous media. The method is mild and tolerant to air, moisture, and a wide range of functional groups, providing a novel way to access a variety of aminated products. Secondary amines like heteroaromatic amines and nucleobases have also been used, affording the corresponding coupling products in good to excellent yields. Moreover, this method has been employed for chemoselective C-N arylation of aminophenols and further utilized for the synthesis of carbazole natural products, avoiding the protection and deprotection steps.

Synthesis of Methylene-Bridged Biscarbazole Alkaloids by using an Ullmann-type Coupling: First Total Synthesis of Murrastifoline-C and Murrafoline-E

We describe the total synthesis of methylene-bridged biscarbazole alkaloids by using a late-stage Ullmann-type coupling of fully functionalised carbazole subunits. The carbazole derivatives were synthesised via a sequence of palladium(0)- and palladium(II

Synthesis of prenyl- and geranyl-substituted carbazole alkaloids by DIBAL-H promoted reductive pyran ring opening of dialkylpyrano[3,2-a]carbazoles

The DIBAL-H promoted reductive pyran ring opening of dialkylpyrano[3,2-a] carbazoles provides a direct access to a broad range of prenyl- and geranyl-substituted carbazoles. Formation of a pyran ring followed by reductive ring opening represents a new met

Efficient construction of pyrano [3, 2-a]carbazoles: Application to a biomimetic total synthesis of cyclized monoterpenoid pyrano [3, 2-a]carbazole Alkaloids

We have developed a highly efficient route to 2-hydroxy-3-methyl-carbazole (1) via a palladium-catalyzed construction of the carbazole skeleton. Using 1 as relay compound, different methods for annulations of pyran rings by reaction with terpenoid building blocks have been tested. The Lewis acid promoted reaction of 1 with prenal (21) opened up an efficient route to girinimbine (3) and the corresponding reaction with citral (25) afforded mahanimbine (5). Oxidation of compounds 3 and 5 provided murraya-cine (4) and murrayacinine (6). Following the biogenetic proposal, mahanim-bine (5) has been exploited for efficient biomimetic syntheses of the cyclized monoterpenoid pyrano[3, 2-a]carbazole alkaloids cyclomahanimbine (7), maha-nimbidine (8) and bicyclomahanimbine (9). The interconversions of 5, 7, 8 and 9 are described and mechanistic implications are discussed. Structural assignments are unambiguously verified by X-ray crystal structure determinations. Moreover, cyclomahanimbine (7) was transformed into murrayazolinine (10) and exozoline (11).

Efficient iron-mediated approach to pyrano[3,2-a]carbazole alkaloids - First total syntheses of O-methylmurrayamine A and 7-methoxymurrayacine, first asymmetric synthesis and assignment of the absolute configuration of (-)-trans-dihydroxygirinimbine

Iron-mediated oxidative cyclisation provides an efficient approach to pyrano[3,2-a]carbazole alkaloids. Thus, improved routes to girinimbine and murrayacine as well as the first total syntheses of O-methylmurrayamine A and 7-methoxymurrayacine are reporte

Transition metal complexes in organic synthesis. Part 33. Molybdenum-mediated total synthesis of girinimbine, murrayacine, and dihydroxygirinimbine

A highly convergent total synthesis of the pyrano[3,2-a]carbazole alkaloids girinimbine, murrayacine, and dihydroxygirinimbine has been accomplished using a consecutive molybdenum-mediated C-C- and C-N-bond formation.