Aziridinyl ketones and their cyclic anils. 10. 2,4,6-Triaryl-1,3-diazabicyclo[3.1.0]hex-3-enes

Orlov, V. D.; Kaluski, Z.; Figas, E.; Vorob'eva, N. P.; Bakumenko, A. I.; Yaremenko, F. G.

doi:10.1007/bf00472284

Cited by 3 publications

(3 citation statements)

References 7 publications

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“…Similar features of molecular structure were found also for related compounds 4 6 and 5. 22 Aziridine and pyrazolyne fragments are fused in a cis-type fashion. The H(1)-C(1)-N(2)-Lp (where Lp is lone pair of the nitrogen) torsion angle is 5 in 1, 4 in 2 and 6 in 3.…”

Section: Resultsmentioning

confidence: 99%

Layered crystal structure of bicyclic aziridines as revealed by analysis of intermolecular interactions energy

et al. 2010

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An X-ray diffraction study of three bicyclic aziridines (2,2-dimethyl-4,6-diaryl-1,3-diazabicyclo-[3.1.0]hex-3-enes) reveals the absence of strong specific intermolecular interactions in the crystals. Therefore, crystal packing has been analyzed on the basis of quantum-chemical calculations of energy of intermolecular interactions between basic molecules located in the asymmetric part of the unit cell and molecules belonging to its first coordination sphere in the crystal. The analysis of the energy of intermolecular interactions indicates that the crystal structures of bicyclic aziridines are layered. The total energy of the interactions between the basic molecule and other molecules belonging to the layer is significantly higher as compared to the energy of the interactions with molecules of two neighbouring layers.

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Section: Resultsmentioning

confidence: 99%

Layered crystal structure of bicyclic aziridines as revealed by analysis of intermolecular interactions energy

et al. 2010

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“…In 1991, Orlov and his co‐workers demonstrated the synthesis of endo‐ and exo‐ 2,4,6‐triaryl‐l,3‐diazabicyclo[3.1.0]hex‐3‐enes 6 and 7 respectively by passing dry ammonia to the suspension of α,β‐chalcone dibromide 2 i.e 1,3‐diaryl‐2,3‐dibromopropan‐1‐one 1.21 g (3.3 mmole), benzaldehyde 0.7 g (6.69 mmole) and NH 4 Cl 0.1 g. After usual workup crystal of endo‐ and exo‐2,4,6‐triaryl‐l,3‐diazabicyclo[3.1.0]hex‐3‐enes 6 and 7 respectively obtained (Scheme ) …”

Section: Synthetic Protocol Of αβ‐Chalcone Dibromidementioning

confidence: 99%

“…In ). [32] Following their interest in photochromism, Mahmoodi and co-workers documented an elegant approach for synthesis of 1,3-diazabicyclo[3,1,0]hex-3-ene derivatives i.e. 9 and 10.…”

Section: Fused Aziridinesmentioning

confidence: 99%

Synthetic Utilization of α,β‐Chalcone Dibromide In Heterocyclic Chemistry and Stereoselective Debromination

Kamal

Kumar

et al. 2019

ChemistrySelect

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This review article epitomize the different synthetic approaches to synthesize α,β‐chalcone dibromide and their application in developing chemically and biologically relevant heterocyclic compounds. The transformation of α,β‐chalcone dibromide into aziridines, pyrazolines, pyrazoles, isoxazoles, pyridine, pyrimidine, flavanoids, diazepines and other heterocyclic compounds has been described briefly in different categories to highlight the importance of these α,β‐chalcone dibromide as key intermediate in organic chemistry. Stereoselective debromination of α,β‐chalcone dibromides with various metal‐containing reducing agents, metal‐metal salt system, ionic liquid, solvents and photoredox catalyst to their corresponding chalcones is also described.

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Synthesis of polyarene derivatives of fused aziridines by Suzuki–Miyaura cross-coupling

et al. 2007

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Aziridinyl ketones and their cyclic anils. 10. 2,4,6-Triaryl-1,3-diazabicyclo[3.1.0]hex-3-enes

Cited by 3 publications

References 7 publications

Layered crystal structure of bicyclic aziridines as revealed by analysis of intermolecular interactions energy

Layered crystal structure of bicyclic aziridines as revealed by analysis of intermolecular interactions energy

Synthetic Utilization of α,β‐Chalcone Dibromide In Heterocyclic Chemistry and Stereoselective Debromination

Synthesis of polyarene derivatives of fused aziridines by Suzuki–Miyaura cross-coupling

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