The Ring Expansions of Glyceraldehyde-Derived Aziridine-2-carboxylates to Oxazolines Take Place with an Uncommon Regiochemistry

Cardillo, Giuliana; Gentilucci, Luca; Mohr, Galla Pericot

doi:10.1002/1099-0690(200109)2001:18<3545::aid-ejoc3545>3.0.co;2-k

Cited by 22 publications

(11 citation statements)

References 29 publications

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“…The compound crystallised in monoclinic system with space group P 2 1 /c, a = 7.6429 (7), b = 25.433(2), c = 9.9223(8) Å; β = 107.841(3)º, Z = 4 and V = 1835.9(1) Å 3 . The crystal system and structural refinement parameters are shown in Table 1.…”

Section: Crystal Structure Of 3bmentioning

confidence: 99%

Regioselective and Stereospecific Synthesis, Crystal Structure and NMR Assignments of N-[(Z)-1-Oxo-1,3-Diphenylprop-2-en-2-yl]-4-Nitrobenzamide

Samimi

Yamin

2014

Journal of Chemical Research

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Isomerisation of cis and trans N-acyl-2-benzoyl-3-phenylaziridines to the corresponding N-(E ) and N-[(Z )-1-oxo-1-aryl-3phenylprop-2-en-2-yl]-4-benzamide, respectively, in the presence of diethyl thiourea is described. The structure of N-[(Z )-1-oxo-1-phenyl-3-phenylprop-2-en-2-yl]-4-nitrobenzamide is also confirmed by the single crystal X-ray diffraction study. A mechanism for this regiospecific rearrangement is proposed.

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Section: Crystal Structure Of 3bmentioning

confidence: 99%

Regioselective and Stereospecific Synthesis, Crystal Structure and NMR Assignments of N-[(Z)-1-Oxo-1,3-Diphenylprop-2-en-2-yl]-4-Nitrobenzamide

Samimi

Yamin

2014

Journal of Chemical Research

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“…Reactions of aziridines 170 and 171 were shown to involve no intermediates (Scheme 100). Neighboring group assistance in the reaction with aziridine 172 was discussed in [199,207] (Scheme 101).…”

Section: 5-dihydro-13-oxazolesmentioning

confidence: 99%

Five-membered oxaza heterocyclic compounds on the basis of epoxides and aziridines

2011

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“…Various aziridines are isomerized by the different conditions such as thermal or non-thermal, [1][2][3] acids or nucleophilic reagents [4][5][6][7][8] and/or photochemical [9,10]. The isomerization of the aziridines are strongly influenced by the nature of the substituents present in them Since the spectral data (e.g., 1 H and 13 Cnmr, ir, and elemental analysis) were not conclusive to assign the stereochemistry of the product, X-ray crystallographic analysis was conducted on 3 to verify product structure.…”

Section: Introductionmentioning

confidence: 99%

Regio- and stereo-synthesis, crystal structure and NMR assignments of N-((Z)-1-oxo-1-phenyl-3-(4-chlorophenyl)prop-2-en-2-yl)-4-nitrobenzamide

Samimi

2015

J IRAN CHEM SOC

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and also the conditions employed [11,12]. Although a large variety of 1-Aroylaziridines are known to be readily isomerized into oxazolines under different conditions, [13][14][15][16][17][18] a literature survey reveals that a few examples of the isomerization of the 2-aryl keto-aziridines has been reported up to now [19][20][21][22]. Padwa and co-worker reported a pyrolytic rearrangement of trans-1,3-dibenzoyl-2-phenyl aziridine in xylene by an initial C-C bond cleavage of the aziridine ring to give a 1,3-dipolar intermediate, which rearranges to give 1,4-diphenyl-4-benzoyloxy-2-azabutadiene via a benzoyl migration (Scheme 1) [2].Our interest in the transformation of the aziridine ring [23-28] to oxazoles, thiazoles, alkenes via C-N bond or C-C bond cleavage, motivated our studies in the isomerizaton of 1,2-diaroyl-3-aryl aziridines to the derivatives of N-((Z)-1-oxo-1,3-diphenylprop-2-en-2-yl) benzamide by a C-N bond cleavage in a regioisomeric manner.The present paper describes regio-and stereo-controlled isomerization of 1,2-diaroyl-3-arylaziridines to the corresponding N-((Z)-1-oxo-1,3-diphenylprop-2-en-2-yl) benzamido in the presence of diethyl thiourea in room temperature. Results and discussionWe prepared trans-2-benzoyl-3-(4-chlorophenyl) aziridines (1) via Gabriel-Cromwell procedure [22]. Then 4-nitrobenzoyl chloride were added to a solution of trans-2-benzoyl-3-(4-chlorophenyl) aziridines (1) in the presence of Et 3 N in CH 2 Cl 2 at 0 °C to furnish 2-benzoyl-1-(4-nitrobenzoyl)-3-(4-chlorophenyl) aziridines (2) which was treated with diethyl thiourea in CH 2 Cl 2 . The reaction afforded the desired product (3) (Scheme 2) (95 %). Abstract Regio and stereo-controlled rearrangement of N-4-nitrophenyl-2-benzoyl-3-(4-Cl phenyl) aziridine to N-((Z)-1-oxo-1-phenyl-3-(4-chlorophenyl)prop-2-en-2-yl)-4 nitrobenzamide is described. The studies on the single crystal X-ray diffraction method confirmed the stereochemistry of the product and the proposed mechanism. The product was crystallized in yellow crystal 0.30 × 0.10 × 0.10 mm, a = 10.0267 (5) Å, b = 16.1419 (9) Å, c = 23.9254 (14) Å, V = 3872.3(4) Å 3 , ρ(calcd) = 1.396 mg cm −3 , μ = 0.229 mm −1 , Z = 8, λ = 0.71073 Å, T = 301 K, ω and ϕ scans, 3591 reflections collected (±h, ±k, ±l), [I ≥ 2 σ(I)], 1959 independent (R int = 0.0808) and 1852 observed reflections [I ≥ 2 σ(I)], 267 refined parameters, R = 0.0544, wR 2 = 0.1260, max residual electron density 0.251 (−0.373) e Å −3 , Flack parameter 0.0040 (6).

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The Ring Expansions of Glyceraldehyde-Derived Aziridine-2-carboxylates to Oxazolines Take Place with an Uncommon Regiochemistry

Cited by 22 publications

References 29 publications

Regioselective and Stereospecific Synthesis, Crystal Structure and NMR Assignments of N-[(Z)-1-Oxo-1,3-Diphenylprop-2-en-2-yl]-4-Nitrobenzamide

Regioselective and Stereospecific Synthesis, Crystal Structure and NMR Assignments of N-[(Z)-1-Oxo-1,3-Diphenylprop-2-en-2-yl]-4-Nitrobenzamide

Five-membered oxaza heterocyclic compounds on the basis of epoxides and aziridines

Regio- and stereo-synthesis, crystal structure and NMR assignments of N-((Z)-1-oxo-1-phenyl-3-(4-chlorophenyl)prop-2-en-2-yl)-4-nitrobenzamide

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