Reduction of 2-phenyl-3a,4,7,7a-tetrahydro-1H-isoindole-1,3(2H)-dione with NaBH4: Investigation of exo-selectivity and reaction mechanism via theoretical computations

被引：0

作者：

Gundogdu, Ozlem ^{[1
,4
]}

Atalay, Abdurrahman ^{[2
,3
]}

Turhan, Pinar ^{[4
]}

Anil, Baris ^{[4
]}

Sahin, Ertan ^{[4
]}

Bozkaya, Ugur ^{[2
]}

Kishali, Nurhan H. ^{[4
]}

Kara, Yunus ^{[4
]}

机构：

[1] Ahi Evran Univ, Kaman Vocat Sch, Dept Food Technol, Kirsehir, Turkiye

[2] Hacettepe Univ, Fac Sci, Dept Chem, Ankara, Turkiye

[3] Avrasya Univ, Fac Hlth Sci, Dept Nutr & Dietet, TR-61080 Trabzon, Turkiye

[4] Ataturk Univ, Fac Sci, Dept Chem, Erzurum, Turkiye

来源：

JOURNAL OF MOLECULAR STRUCTURE | 2025年 / 1319卷

关键词：

3-hydroxylactam; Acylaminocarbinol; Metal hydride reduction; Bicyclic imide; Theoretical computations; CONVENIENT SYNTHESIS; PHTHALIMIDES; DERIVATIVES; CONVERSION; CANTHARIMIDE; ANALOGS;

D O I：

10.1016/j.molstruc.2024.139520

中图分类号：

O64 [物理化学（理论化学）、化学物理学];

学科分类号：

070304 ; 081704 ;

摘要：

The reaction of the bicyclic imide with NaBH4 afforded acylaminocarbinol and carboxamide derivatives. The exact configuration of acylaminocarbinol 7 was determined by X-ray crystal analysis. Theoretical studies were carried out to explain the mechanism of the exo-selectivity observed in the first step of the reduction reaction and the formation of the secondary product in the second step. According to the obtained findings, i) in the first step of the reaction, the exo-path is kinetically more favorable, and ii) an alternative mechanism has been proposed instead of the mechanism proposed in the literature. The canonical forms of the amide group in the lactam ring were found to make an important contribution to the mechanism. iii) The amount of products formed in the reduction reaction depends on the reaction conditions.

引用

页数：7

共 50 条

[11] Reaction of 7-phenyl-7H-pyrazolo-[3,4-d][1,2,3]triazin-4-ol with thionyl chloride
Khutova, B. M.
Klyuchko, S. V.
Gurenko, A. O.
Vasilenko, A. N.
Rusanov, E. B.
Brovarets, V. S.
CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2013, 49 (06) : 922 - 929
[12] Halocyclization of 2-(2-{4-[allylamino(thioxo)methyl]piperazin-1-yl}ethyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione
Zborovskii, Yu. L.
Orysyk, V. V.
Staninets, V. I.
Bon', V. V.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2011, 47 (06) : 881 - 885
[13] Crystal structure of 2-phenyl-5,6,7,8-tetrahydro-4H-benzo[4,5]thieno[2,3-d][1,3]oxazin-4-one, C16H13NO2S
Ghabbour, Hazem A.
ZEITSCHRIFT FUR KRISTALLOGRAPHIE-NEW CRYSTAL STRUCTURES, 2016, 231 (02): : 623 - 625
[14] Multivariate regression with substituent shift increments.: IV.: 2-(4-X-phenyl)-1,3-dihydro-2H-isoindole-1,3-diones and 3-(4-X-Penyl)-3,4-dihydro-2H-1,3-benzoxazine-2,4-diones
Holík, M
Friedl, Z
Waisser, K
Gregor, J
COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 1999, 64 (10) : 1709 - 1726
[15] SOLVENT-FREE MICROWAVE ASSISTED SYNTHESIS AND ANTIMICROBIAL ACTIVITY OF NEW 2-{4-[3-(1-PHENYL-3-ARYL-1H-PYRAZOL-4-YL)-ACRYLOYL]-PHENYL}-ISOINDOLE-1,3-DIONES
Ashok, D.
Ganesh, Arram
Ravi, S.
Lakshmi, B. Vijaya
INDIAN JOURNAL OF HETEROCYCLIC CHEMISTRY, 2014, 24 (01) : 29 - 34
[16] An efficient synthesis of 1,3-dimethyl-5-(2-phenyl-4H-chromen-4-ylidene) pyrimidine-2,4,6(1H,3H,5H)-triones and investigation of their interactions with β-lactoglobiulin
Sepay, Nayim
Mallik, Sumitava
Guha, Chayan
Mallik, Asok K.
RSC ADVANCES, 2016, 6 (98) : 96016 - 96024
[17] Convenient selective synthesis of 5,7,8,9-tetrahydro-4H,6H-chromeno[2,3-d][1,3]oxazin-4-ones
Litvinov, Yu. M.
Shestopalov, A. M.
RUSSIAN CHEMICAL BULLETIN, 2009, 58 (02) : 479 - 481
[18] 2-(6-Phenyl-7H-1,2,4-triazolo[3,4-b][1,3,4]thiadiazin-3-yl)-1,3-benzothiazole
Abdel-Aziz, Hatem A.
Ng, Seik Weng
Tiekink, Edward R. T.
ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2011, 67 : O2610 - U2175
[19] Reactions of 1,3-Diphenl-2-pyrazolin-5-one and 4-Amino-1,5-dimethyl-2-phenyl-1H-pyrazol-3(2H)-one. Synthesis of Some New Pyrazoles and Pyrazolones
El-Metwally, Souad
Khalil, Ali Kh.
ACTA CHIMICA SLOVENICA, 2010, 57 (04) : 941 - 947
[20] Palladium-Catalyzed Decarboxylative Synthesis of 5H-Benzo[4,5][1,3]oxazino[2,3-a]isoindole-5,11(6aH)-Diones using 2-Phenyl-4H-Benzo[d][1,3]oxazin-4-Ones and α-Oxo Carboxylic Acids
Lalji, Ram Sunil Kumar
Kumar, Prashant
Gupta, Mohit
Parmar, Virinder S.
Singh, Brajendra K.
ADVANCED SYNTHESIS & CATALYSIS, 2020, 362 (03) : 552 - 560

← 1 2 3 4 5 →