1122-09-4

Usage

Uses

Used in Pharmaceutical Industry:
3-Azabicyclo[3.2.0]heptane-2,4-dione is utilized as a key intermediate in the synthesis of a range of pharmaceuticals. Its unique structure allows for the creation of diverse drug molecules, contributing to the development of new therapeutic agents.
Used in Organic Synthesis:
In the field of organic synthesis, 3-Azabicyclo[3.2.0]heptane-2,4-dione is employed as a building block for the construction of heterocyclic compounds. Its ability to form multiple bonds and participate in various chemical reactions makes it a valuable component in the synthesis of complex organic molecules.
Used as a Precursor for Nitrogen-Containing Compounds:
3-Azabicyclo[3.2.0]heptane-2,4-dione also serves as a precursor in the synthesis of other nitrogen-containing compounds. Its presence in these compounds can influence their reactivity and properties, making it an important starting material in the preparation of various nitrogen-based chemicals.
Used in the Development of New Therapeutic Agents:
Due to its potential biological activity, 3-Azabicyclo[3.2.0]heptane-2,4-dione is of interest in the research and development of innovative therapeutic agents. Its incorporation into new drug molecules could lead to the discovery of treatments for a variety of medical conditions.

InChI:InChI=1/C6H7NO2/c8-5-3-1-2-4(3)6(9)7-5/h3-4H,1-2H2,(H,7,8,9)

Upstream product

• 4462-96-8 cis-1,2-cyclobutane dicarboxylic anhydride 
• 541-59-3 maleiimide 
• 74-85-1 ethene 

Downstream Products

• 192824-73-0 (1S,4S,5R)-3-Benzyl-4-hydroxy-3-aza-bicyclo[3.2.0]heptan-2-one 

Relevant academic research and scientific papers

Finding the Perfect Match: A Combined Computational and Experimental Study toward Efficient and Scalable Photosensitized [2 + 2] Cycloadditions in Flow

With ever-evolving light-emitting diode (LED) technology, classical photochemical transformations are becoming accessible with more efficient and industrially viable light sources. In combination with a triplet sensitizer, we report the detailed exploration of [2 + 2] cycloadditions, in flow, of various maleic anhydride derivatives with gaseous ethylene. By the use of a flow reactor capable of gas handling and LED wavelength/power screening, an in-depth optimization of these reactions was carried out. In particular, we highlight the importance of matching the substrate and sensitizer triplet energies alongside the light source emission wavelength and power. Initial triplet-sensitized reactions of maleic anhydride were hampered by benzophenone's poor absorbance at 375 nm. However, density functional theory (DFT) calculations predicted that derivatives such as citraconic anhydride have low enough triplet energies to undergo triplet transfer from thioxanthone, whose absorbance matches the LED emission at 375 nm. This observation held true experimentally, allowing optimization and further exemplification in a larger-scale reactor, whereby >100 g of material was processed in 10 h. These straightforward DFT calculations were also applied to a number of other substrates and showed a good correlation with experimental data, implying that their use can be a powerful strategy in targeted reaction optimization for future substrates.

Finding the Perfect Match: A Combined Computational and Experimental Study toward Efficient and Scalable Photosensitized [2 + 2] Cycloadditions in Flow

With ever-evolving light-emitting diode (LED) technology, classical photochemical transformations are becoming accessible with more efficient and industrially viable light sources. In combination with a triplet sensitizer, we report the detailed exploration of [2 + 2] cycloadditions, in flow, of various maleic anhydride derivatives with gaseous ethylene. By the use of a flow reactor capable of gas handling and LED wavelength/power screening, an in-depth optimization of these reactions was carried out. In particular, we highlight the importance of matching the substrate and sensitizer triplet energies alongside the light source emission wavelength and power. Initial triplet-sensitized reactions of maleic anhydride were hampered by benzophenone's poor absorbance at 375 nm. However, density functional theory (DFT) calculations predicted that derivatives such as citraconic anhydride have low enough triplet energies to undergo triplet transfer from thioxanthone, whose absorbance matches the LED emission at 375 nm. This observation held true experimentally, allowing optimization and further exemplification in a larger-scale reactor, whereby >100 g of material was processed in 10 h. These straightforward DFT calculations were also applied to a number of other substrates and showed a good correlation with experimental data, implying that their use can be a powerful strategy in targeted reaction optimization for future substrates.

The synthesis of unsubstituted cyclic imides using hydroxylamine under microwave irradiation

Unsubstituted cyclic imides were synthesized from a series of cyclic anhydrides, hydroxylamine hydrochloride (NH2OH·HCl), and 4-N,N-dimethylamino-pyridine (DMAP, base catalyst) under microwave irradiation in monomode and multimode microwaves. This novel microwave synthesis produced high yields of the unsubstituted cyclic imides for both the monomode (61-81%) and multimode (84-97%) microwaves.

Nonreductive enantioselective ring opening of N-(methylsulfonyl)dicarboximides with diisopropoxytitanium α,α,α′,α′-tetraaryl-1,3-dioxolane-4,5- dimethanolate

The bicyclic and tricyclic meso-N-(methylsulfonyl)dicarboximides 1a-f are converted enantioselectively to isopropyl [(sulfonamido)carbonyl]-carboxylates 2a-f by diisopropoxytitanium TADDOLate (75-92% yield; see Scheme 3). The enantiomer ratios of the products are between 86:14 and 97:3, and recrystallization from CH2Cl2/hexane leads to enantiomerically pure sulfonamido esters 2 (Scheme 3). The enantioselectivity shows a linear relationship with the enantiomer excess of the TADDOL employed (Fig. 3). Reduction of the ester and carboxamide groups (LiAlH4) and additional reductive cleavage of the sulfonamido group (Red-Al) in the products 2 of imide-ring opening gives hydroxy-sulfonamides 3 and amino alcohols 4, respectively (Scheme 4). The absolute configuration of the sulfonamido esters 2 is determined by chemical correlation (with 2a, b; Scheme 6), by the X-ray analysis of the camphanate of 3e (Fig. I), and by comparative 19F-NMR analysis of the Mosher esters of the hydroxy-sulfonamides 3 (Table I). A general proposal for the assignment of the absolute configuration of primary alcohols and amines of Formula HXCH2CHR1R2, X = O, NH, is suggested (see 11 in Table I). It follows from the assignment of configuration of 2 that the Re carbonyl group of the original imide 1 is converted to an isopropyl ester group. This result is compatible with a rule previously put forward for the stereochemical course of reactions involving titanium TADDOLate activated chelating electrophiles (12 in Scheme 7). A tentative mechanistic model is proposed (13 and 14 in Scheme 7).

OLEFIN CYCLISATIONS OF HINDERED α-ACYLIMINIUM IONS

Stereocontrolled NaBH4/H+-reduction of 3,4-cis-disubstituted N-alkenyl imides 1-5 leads to secondary hydroxylactams.Tertiary hydroxylactams are formed via addition of MeMgCl to imides 2 and 4.HCOOH-Cyclisation of the hydroxylactams affords polycyclic piperidines through stereoselective α-acyliminium ring closure.Concomitant synchronous and stepwise cyclisation pathways are operative in the anti-periplanar addition of tertiary α-acyliminium ions to Me substituted olefins 8c and 11c.