Preparation of amidines from gem-dichloroaziridines

Meilahn, Marcus K.; Augenstein, Larry L.; McManaman, James L.

doi:10.1021/jo00822a038

Cited by 20 publications

(10 citation statements)

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“…Yield 92%, oil; 1 H NMR (500 MHz, CDCl 3 ) d 6.92 (1H, s, 2H-Ar), 7.24 (1H, dd, J¼8.0 Hz, 5H-Ar), 7.03 (1H, d, J¼8.0 Hz, Ar), 6.85 (1H, d, J¼8.0 Hz, Ar), 2.84 (s, 6H, NMe 2 ), 2.68 (12H, d, J¼11.0 Hz, NMe 2 ); 13 C NMR (125 MHz, CDCl 3 ) d 152.6 (d, J¼146.0 Hz), 150.4 (d, J¼19.0 Hz), 126.4 (q, J¼272.0 Hz), 130.7 (q, J¼31.4 Hz), 128.8, 123.4, 117.5 (d, J¼3.8 Hz), 116.7 (d, J¼3.8 Hz), 41.1, 37.9; 31 P NMR (81 MHz, CDCl 3 ) d 64.0; 19 F NMR (188 MHz, CDCl 3 ) d À63.0. [Found:C, 40.54; N, 13.71; P, 7.53. C 14 H 22 F 3 N 4 PSe requires C, 40.69; N, 13.56; P, 7.49].…”

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confidence: 99%

Convenient method for the synthesis of C-phosphorylated N-arylformamidines

et al. 2010

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confidence: 99%

Convenient method for the synthesis of C-phosphorylated N-arylformamidines

et al. 2010

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“…The presence of heteroatoms on the ring has been observed to affect the reactivity of the aziridines in such a way that in many cases compounds can be transformed into other aziridine derivatives, whereas in other cases the ring undergoes cleavage affording diverse types of interesting products. From a biological point of view, they serve as precursors for the synthesis of biologically active compounds such as indolinones,15b analogues of natural alkaloids such as isoquinolinones15c and isoquinolines,15d and amidines 15e. Currently, the most common method for the synthesis of 2,2‐dichloroaziridines comprises dichlorocarbene‐imine addition 16.…”

Section: Methodsmentioning

confidence: 99%

OC094: Outcome of trichorionic triplet pregnancies at 10-14 weeks after embryo reduction compared to expectant management

Papageorghiou

Liao

Skentou

et al. 2003

Ultrasound Obstet Gynecol

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Introduction: 3D ultrasound technology offers the ability to demonstrate the fetal face in three different display modes: the multiplanar, the surface and the transparent mode. Material and Methods: In 2012 cases the fetal face was assessed with 2D and 3D ultrasound as part of a level III screening evaluation for fetal anomalies. The ultrasound equipment used was a Voluson 530 MT or a Voluson 730 from GE-Kretztechnik, Austria. In every fetus a volume of the face was acquired and stored on a rewritable magneto optical disk (540 MB). Results: The simultaneous display of all three orthogonal sectional planes enables us to define the true facial profile and to review the fetal face in a systematic tomographic survey. The surface view allows a clear demonstration of surface anomalies such as facial dysplasia, cyclopia with proboscis, cleft lip and palate or retrognathia. The translucency mode provides a complete survey of the fetal skull and the facial bones, similar to the appearance of an X-ray film. With the latest 4D ultrasound technology of Voluson 730 the fetus can be visualized three-dimensionally in real time. This gives the examiner a direct access to facial movements such as grimacing, yawning or swallowing. In 67 of the 2012 fetuses facial anomalies were detected. Comparing 2D and 3D ultrasound results, 3D ultrasound provided superior image quality and revealed the anomalies more conclusively in 73% of the fetuses. Summary: 3D ultrasound does not only enable a precise demonstration of subtle malformations of the fetal face, but can also provide more convincing evidence of a normal fetal face than 2D sonograms. OC094 Outcome of trichorionic triplet pregnancies at 10-14 weeks after embryo reduction compared to expectant management

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“…2,2-Dichloro-1,3-diphenylaziridine (2a), 2 S5 2,2-dichloro-1-(1-naphthyl)-3-phenylaziridine (2b), 3 1-benzyl-2,2-dichloro-3,3-diphenylaziridine (2c) 3 and N-benzyl-α-chlorophenylacetamide (3g) 4 were identified by comparison of their data ( 1 H NMR, IR and mp) with those in the literature.…”

Section: 2-dichloroaziridines 2a-c and N-benzyl-α-chlorophenylacetamide (3g)mentioning

confidence: 99%

Novel Synthesis of gem‐Dichloroaziridines from Imines via the KF/Al₂O₃‐Promoted Generation of Dichlorocarbene from Chloroform.

Mihara¹,

Ishino²,

Minakata³

et al. 2005

ChemInform

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The KF/Al2O3-promoted reaction of in situ generated dichlorocarbene with imines (I) and (IV) is tolerant to various functional groups like cyano, nitro groups or double bonds. In the case of imines (IV), the reaction does not stop at the stage of dichloroaziridines [cf. (III)] but gives the corresponding hydrolysis products (V). -(MIHARA, M.; ISHINO*, Y.; MINAKATA, S.; KOMATSU, M.; J. Org. Chem. 70 (2005) 13, 5320-5322; Osaka Munic. Tech. Res. Inst., Joto, Osaka 536, Japan; Eng.) -Mischke 45-125

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Preparation of amidines from gem-dichloroaziridines

Cited by 20 publications

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Convenient method for the synthesis of C-phosphorylated N-arylformamidines

Convenient method for the synthesis of C-phosphorylated N-arylformamidines

OC094: Outcome of trichorionic triplet pregnancies at 10-14 weeks after embryo reduction compared to expectant management

Novel Synthesis of gem‐Dichloroaziridines from Imines via the KF/Al₂O₃‐Promoted Generation of Dichlorocarbene from Chloroform.

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Preparation of amidines from gem-dichloroaziridines

Cited by 20 publications

References 0 publications

Convenient method for the synthesis of C-phosphorylated N-arylformamidines

Convenient method for the synthesis of C-phosphorylated N-arylformamidines

OC094: Outcome of trichorionic triplet pregnancies at 10-14 weeks after embryo reduction compared to expectant management

Novel Synthesis of gem‐Dichloroaziridines from Imines via the KF/Al2O3‐Promoted Generation of Dichlorocarbene from Chloroform.

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Novel Synthesis of gem‐Dichloroaziridines from Imines via the KF/Al₂O₃‐Promoted Generation of Dichlorocarbene from Chloroform.