Experimental and theoretical study on diethyl-(Z)-2-(5,7-diphenyl-1,3,4-oxadiazepin-2-yl)-2-butenedioate using different levels of computational methods

Asadi, Zahra; Asnaashariisfahani, Manzarbanou; Vessally, Esmail; Esrafili, Mehdi D.

doi:10.1016/j.saa.2014.11.105

Cited by 13 publications

(7 citation statements)

References 25 publications

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“…These libraries can then be tested with enzymes or living organisms to find new active pharmaceutical substances. As a continuation our recent studies (23)(24)(25)(26), we report the green MCR between (L)-α-amino acids, aromatic aldehydes and p-toluenesulfonylmethyl isocyanide in water/methanol ( Figure 1).…”

Section: Introductionsupporting

confidence: 79%

A novel multicomponent reaction between amino acids, aromatic aldehydes andp-toluenesulfonylmethyl isocyanide: an efficient and green one-pot synthesis using nanosilica

Edjlali

Vessally

Jafari

et al. 2016

Green Chemistry Letters and Reviews

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The novel diastereomeric sulfonylamide derivatives 4a-h were synthesized by multi-component reactions between (L)-α-amino acids, 1, aromatic aldehydes, 2 and p-toluenesulfonylmethyl isocyanide, 3 in water/methanol using nanosilica as a catalyst. The one-pot green reactions were carried out at room temperature with a quantitative yield in water/methanol. The yield of the reactions and products was determined and discussed. The reusablity of the catalyst is discussed.

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Section: Introductionsupporting

confidence: 79%

A novel multicomponent reaction between amino acids, aromatic aldehydes andp-toluenesulfonylmethyl isocyanide: an efficient and green one-pot synthesis using nanosilica

Edjlali

Vessally

Jafari

et al. 2016

Green Chemistry Letters and Reviews

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“…Heteroaryl carboxylic acids could be employed, showcasing the tolerance of the reaction to the presence of Lewis basic functionalities, producing 9-11. Carboxylic acids bearing electrophilic substituents including; aldehydes (12), sulfonyl fluorides (13), trifluoromethyl alkenes ( 14), allyl bromides (15), and alkyl bromides (16), acted as efficient coupling partners providing products with additional sites for further nucleophilic functionalization. Pyruvic acid (17), and an oxalic acid half ester (18) reacted successfully affording acyl a-amino 1,3,4-oxadiazoles in 48 % and 57 % yield, respectively.…”

mentioning

confidence: 99%

“…[15] A 1,3-dicarbonyl compound (1,3diphenyl-1,3-propanedione) proved suitably acidic allowing facile access to a unique a-amino 1,3,4-oxadiazepine scaffold (22). [16] Our investigation of N-H Brønsted acids started with use of 4-hydroxyquinazoline and gave the a-amino [1,2,4]triazolo [4,3-c]quinazoline (23) in 33 % yield. [17] Building upon this result, N-acyl sulfonamides (24) and N-acyl carbamates (25) were reacted to afford N-functionalized aamino 1,2,4-triazoles.…”

mentioning

confidence: 99%

General α‐Amino 1,3,4‐Oxadiazole Synthesis via Late‐Stage Reductive Functionalization of Tertiary Amides and Lactams**

Matheau‐Raven

Dixon

2021

Angew Chem Int Ed

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An iridium-catalyzed reductive three-component coupling reaction for the synthesis of medicinally relevant α-amino 1,3,4-oxadiazoles from abundant tertiary amides or lactams, carboxylic acids, and (N-isocyanimino) triphenylphosphorane, is described. Proceeding under mild conditions using (<1 mol%) Vaska's complex (IrCl(CO)(PPh 3) 2 ) and tetramethyldisiloxane to access the key reactive iminium ion intermediates, a broad range of structurally complex α-amino 1,3,4-oxadiazole architectures were efficiently accessed from diverse carboxylic acid feedstock coupling partners. Extension to α-amino heterodiazole synthesis was readily achieved by exchanging the carboxylic acid coupling partner for C-, S-, or N-centered Brønsted acids, and provided rapid and modular access to these desirable, yet difficult-to-access, heterocycles. Furthermore, the high chemoselectivity of the catalytic reductive activation step allowed the late-stage functionalization of 10 drug molecules, including the synthesis of novel heterodiazole-fused drug-drug conjugates. File list (2) download file view on ChemRxiv VaskaOxadiazoles -ChemRxiv.pdf (1.02 MiB) download file view on ChemRxiv VaskaOxadiazolesSI.pdf (4.98 MiB)

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“…The aromatic ring C-C vibrations usually occurs in the region of 1600-1400 cm −1 [37,38]. In the present case, the C-C stretching vibrations have been assigned 725 (mode no.…”

Section: C-c Vibrationsmentioning

confidence: 59%

“…In present case, the in-plane bending of phenyl ring computed at 1533, 1317, 1191, and 1179 cm −1 (for PBE1PBE/6-311+G(2d,p) matches with 1525, 1307, 1199, and 1168 cm −1 in IR spectrum (mode no. 24,33,37,38). The PED, these modes involve the contribution of 17, 26, 28, and 28%.…”

Section: C-h Vibrationsmentioning

confidence: 99%

Vibrational studies, NMR analysis, modeling of electronic and thermodynamical parameters of 1,3-bis(4-benzamido)triazene

Ghalebsaz-Jeddi

Vessally

2016

Russ. J. Phys. Chem.

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The optimized geometry, vibrational wavenumbers, 1 H and 13 C chemical shift values of 1,3-bis(4benzamido)triazene, BBT, in the ground state were computed with the Hartree-Fock (HF) and density functional theory method (PBE1PBE) with 6-311+G(2d,p) basis set. The harmonic vibrational wavenumbers of BBT were calculated and the scaled values were compared with the experimental FT-IR spectra. A detailed interpretation of the NMR spectra of BBT was reported. The calculated data are in reasonably good agreement with experimental measurements. Moreover, the log P value was estimated with ChemBioOffice Ultra 11.0, ACD/LogP, and ALOGPS programs.

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Experimental and theoretical study on diethyl-(Z)-2-(5,7-diphenyl-1,3,4-oxadiazepin-2-yl)-2-butenedioate using different levels of computational methods

Cited by 13 publications

References 25 publications

A novel multicomponent reaction between amino acids, aromatic aldehydes andp-toluenesulfonylmethyl isocyanide: an efficient and green one-pot synthesis using nanosilica

A novel multicomponent reaction between amino acids, aromatic aldehydes andp-toluenesulfonylmethyl isocyanide: an efficient and green one-pot synthesis using nanosilica

General α‐Amino 1,3,4‐Oxadiazole Synthesis via Late‐Stage Reductive Functionalization of Tertiary Amides and Lactams**

Vibrational studies, NMR analysis, modeling of electronic and thermodynamical parameters of 1,3-bis(4-benzamido)triazene

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