A facile synthesis of 1,1-disubstituted isoindoline derivatives by intramolecular iodoamination of 2-vinylbenzylamine derivatives

被引：8

作者：

Kobayashi, Kazuhiro ^{[1
]}

Kondo, Shizuka ^{[1
]}

Hashimoto, Kenichi ^{[1
]}

Fukamachi, Shuhei ^{[1
]}

Morikawa, Osamu ^{[1
]}

Konishi, Hisatoshi ^{[1
]}

机构：

[1] Tottori Univ, Fac Engn, Dept Mat Sci, Tottori 6808552, Japan

来源：

HETEROCYCLES | 2007年 / 71卷 / 08期

关键词：

iodine; iodoamination; isoindoline; sodium thiolate; 2-vinylbenzylamine;

D O I：

10.3987/COM-07-11072

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The intramolecular iodoamination of N-(2-vinylbenzyl)acetamide derivatives, derived from cc-substituted 2-vinylbenzonitriles in two steps, afforded the corresponcling 2-acetyl-1-iodomethylisoindoline derivatives, which were transformed into the 1-methyl or 1-Sulfenylmethyl derivatives by tributyltin hydride reduction or substitution by sodium thiolates, respectively, in reasonable yields.

引用

页码：1827 / 1835

页数：9

共 50 条

[21] Synthesis, Molecular Modeling, Anticonvulsant and Antinociceptive Properties of New 1,1-Disubstituted Cyclohexane and 1,3-Diazaspiro[4.5]decane Derivatives
Aboul-Enein, Mohamed Nabil
El-Azzouny, Aida A.
Ragab, Fatma
Abdel-Maksoud, Mohammed S.
Abd-Allah, Walaa H.
Maklad, Yousreya
CHEMISTRYSELECT, 2019, 4 (04): : 1360 - 1365
[22] Electrifying Friedel-Crafts Intramolecular Alkylation toward 1,1-Disubstituted Tetrahydronaphthalenes
Lunghi, Enrico
Ronco, Pietro
Della Negra, Federico
Trucchi, Beatrice
Verzini, Massimo
Merli, Daniele
Casali, Emanuele
Kappe, C. Oliver
Cantillo, David
Zanoni, Giuseppe
JOURNAL OF ORGANIC CHEMISTRY, 2023, 88 (24): : 16783 - 16789
[23] ISOINDOLINE DERIVATIVES .3. SYNTHESIS OF 1,1-DIMETHYL-2N-PHENYL-3-METHYLENEISOINDOLINE
FABRYCY, A
KOSMIDER, A
ROCZNIKI CHEMII, 1974, 48 (06): : 1069 - 1071
[24] Synthesis of 1,1-disubstituted tetrahydro-β-carbolines from 2-methyleneaziridines
Mumford, Peter M.
Shiers, Jason J.
Tarver, Gary J.
Hayes, Jerome F.
Shipman, Michael
TETRAHEDRON LETTERS, 2008, 49 (21) : 3489 - 3491
[25] CHIRAL FORMAMIDINES - ASYMMETRIC-SYNTHESIS OF 1,1-DISUBSTITUTED TETRAHYDROISOQUINOLINES
MEYERS, AI
GONZALEZ, MA
STRUZKA, V
AKAHANE, A
GUILES, J
WARMUS, JS
TETRAHEDRON LETTERS, 1991, 32 (40) : 5501 - 5504
[26] ORGANOSILICON COMPOUNDS .2. 1,1-DISUBSTITUTED SILACYCLOHEXANES
TAMBORSKI, C
ROSENBERG, H
JOURNAL OF ORGANIC CHEMISTRY, 1960, 25 (02): : 246 - 248
[27] The synthesis of 1,1-disubstituted tetrahydro-β-carbolines induced by iodine
Lingam, Y.
Rao, D. Muralimohan
Bhowmik, Dipal R.
Santu, Pachore Sharad
Rao, K. Raghavendra
Islam, Aminul
TETRAHEDRON LETTERS, 2007, 48 (40) : 7243 - 7245
[28] 1,1-DISUBSTITUTED 2-METHYLCYCLOPROPANES AND 2-METHYLCYCLOBUTANE
GOSSELCK, J
WINKLER, A
TETRAHEDRON LETTERS, 1970, (28) : 2437 - &
[29] Synthesis of 2-hydroxytetrahydrofurans by Wacker-type oxidation of 1,1-disubstituted alkenes
Tanaka, Rina
Komori, Saki
Shimizu, Yuhei
Kataoka, Yasutaka
Ura, Yasuyuki
ORGANIC & BIOMOLECULAR CHEMISTRY, 2022, 20 (03) : 570 - 574
[30] SYNTHESIS AND ANALGESIC EVALUATION OF SOME 1,1-DISUBSTITUTED 3-CARBOXY-4-PHENYL-1,2,3,4-TETRAHYDRO-BETA-CARBOLINE DERIVATIVES
NAGY, T
JEANNIN, L
SAPI, J
LARONZE, JY
RENARD, P
PFEIFFER, B
BIZOTESPIARD, JG
EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 1995, 30 (7-8) : 575 - 586

← 1 2 3 4 5 →