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

[21] Synthesis, characterization, in vitro antimicrobial and QSAR studies of diorganotin(IV) complexes of Schiff bases derived from 2-(3-methylbutanoyl)-1H-indene-1,3(2H)-dione and 4-substituted anilines
Khatkar, Priyanka
Asija, Sonika
Ahlawat, Aarti
Singh, Vikramjeet
MONATSHEFTE FUR CHEMIE, 2019, 150 (02): : 207 - 218
[22] Chemistry of Iminofurans. Recyclization of Ethyl 2-[2-Oxo-5-phenylfuran-3(2H)-ylideneamino]-4,5,6,7-tetrahydro-1-benzothiophene-3-carboxylate in Reaction with Amines
Shipilovskikh, S. A.
Shipilovskikh, D. A.
Rubtsov, A. E.
RUSSIAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 53 (01) : 137 - 140
[23] Crystal structures of 6a,6b,7,11a-tetrahydro-6H,9H-spiro[chromeno[3′,4′:3,4]pyrrolo[1,2-c]-thiazole-11,3′-indoline]-2′,6-dione and 5′-methyl-6a,6b,7,11a-tetrahydro-6H,9H-spiro[chromeno-[3′,4′:3,4] pyrrolo[1,2-c]thiazole-11,3′-indoline]-2′,6-dione
Pangajavalli, S.
Ranjithkumar, R.
Srinivasan, N.
Ramaswamy, S.
Selvanayagam, S.
ACTA CRYSTALLOGRAPHICA SECTION E-CRYSTALLOGRAPHIC COMMUNICATIONS, 2019, 75 : 246 - +
[24] Synthesis and crystal structure of tert-butyl (2′R,3R,3′R,4a′R,9a′S)-1-acetyl-5-chloro-3"-methyl-2,5",9′-trioxo-1"-phenyl-1",4a′,5", 9a′-tetrahydro-1′H,3′H,9′H-dispiro[indoline-3,4′-xanthene-2′,4"-pyrazole]-3′-carboxylate, C36H32ClN3O7
Li, Wu-Wu
Gu, Yuan-Zi
Cao, Lei
ZEITSCHRIFT FUR KRISTALLOGRAPHIE-NEW CRYSTAL STRUCTURES, 2021, 236 (01): : 77 - 80
[25] An efficient one-pot expeditious synthesis of 3-phenyl-1-(6-phenyl-7H-[1,2,4] triazolo[3,4-b] [1,3,4] thiadiazin-3-yl)-1H-pyrazol-5-amines via multicomponent approach
Sujatha, Kodam
Deshpande, Ravindra Pramod
Kesharwani, Rajesh Kumar
Babu, Phanithi Prakash
Vedula, Rajeswar Rao
SYNTHETIC COMMUNICATIONS, 2019, 49 (01) : 49 - 55
[26] Cobalt-Catalyzed Switchable [4+1] and [4+1+1] Spirocyclization of Aromatic Amides with 2-Diazo-1H-indene-1,3(2H)-dione: Access to Spiro Indene-2,1'-isoindolinones and Spiro Isochroman-3,1'-isoindolinones
Li, Bin
Xie, Mengmeng
Li, Jingyu
Shen, Nana
Zhang, Xinying
Fan, Xuesen
CHINESE JOURNAL OF CHEMISTRY, 2024, 42 (04) : 363 - 369
[27] Green Construction of Novel 3-(Benzo[d][1,3]dioxol-5-yl)-1,8-naphthyridin-2-yl)amino)quinazoline-2,4(1H,3H)-dione and Phenyl-[1,2,4]triazolo[4,3-a][1,8]naphthyridine and Their Antimicrobial Activity
Reddy, Sontireddy Surender
Shireesha, Kavati
Jella, Kumara Swamy
JOURNAL OF HETEROCYCLIC CHEMISTRY, 2024, : 122 - 129
[28] Synthesis, Structural Investigation, Antiphospholipases, Antiproteases and Antimicrobial Activities of 2-(4-hydroxy-3-methoxy-benzylidene)-6-methoxy-3,4-dihydro-2H-naphthalen-1-one and 4-(4-hydroxy-3-methoxy-phenyl)-8-methoxy-3,4,5,6-tetrahydro-1H-benzo[h]quinazoline-2-thione
El-Sayed, Nahed N. E.
Almaneai, Norah M.
Soliman, Saied M.
Ben Bacha, Abir
Ghabbour, Hazem A.
JOURNAL OF THE CHEMICAL SOCIETY OF PAKISTAN, 2019, 41 (06): : 1074 - 1089
[29] Synthesis of novel spiro[benzo[4,5]thiazolo[3,2-a]chromeno[2,3-d] pyrimidine-14,3′-indoline]-1,2′,13(2H)-triones via three component reaction
Jannati, Saeideh
Esmaeili, Abbas Ali
TETRAHEDRON, 2018, 74 (24) : 2967 - 2972
[30] Vibrational spectroscopy investigation using ab initio and DFT vibrational analysis of 7-chloro-2-methylamino-5-phenyl-3H-1, 4-benzodiazepine-4-oxide
Prasath, M.
Muthu, S.
Balaji, R. Arun
SPECTROCHIMICA ACTA PART A-MOLECULAR AND BIOMOLECULAR SPECTROSCOPY, 2013, 113 : 224 - 235

← 1 2 3 4 5 →