Synthesis of 5-Substituted 2-Pyrrolidinones by Coupling of Organozinc Reagents with Cyclic N -Acyliminium Ions

被引：1

作者：

Zaragoza-Galicia, Ivann ^{[1
]}

Santos-Sanchez, Zaira A. ^{[1
]}

Hidalgo-Mercado, Yazmin, I ^{[1
]}

Olivo, Horacio F. ^{[1
]}

Romero-Ortega, Moises ^{[1
]}

机构：

[1] Univ Autonoma Estado Mexico, Fac Quim, Dept Quim Organ, Toluca 50180, Mexico

来源：

SYNTHESIS-STUTTGART | 2019年 / 51卷 / 24期

关键词：

N-acyliminium ions; organozinc reagents; coupling reactions; 5-allyl-2-pyrrolidinones; azabicyclic systems; STEREOSELECTIVE ADDITION; AMINO-ACIDS; CONCISE SYNTHESIS; DELTA-LACTAMS; INDOLIZIDINE; CYCLIZATIONS; DERIVATIVES; GENERATION; REDUCTION; CHEMISTRY;

D O I：

10.1055/s-0037-1610733

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A coupling reaction between cyclic N-acyliminium ions with organozinc reagents is described. The cyclic N-acyliminium ions, generated in situ from N-substituted-5-hydroxy-2-pyrrolidinones by treatment with boron trifluoride-diethyl ether complex or titanium tetrachloride, are trapped by the organozinc reagent, which is formed from an alkyl bromide in the presence of zinc in the same reaction medium. The N-substituted-5-allyl-2-pyrrolidinones generated using this method serve as versatile intermediates for the synthesis of azabicyclic systems with indolizidine and pyrroloazepinolizidine cores.

引用

页码：4650 / 4656

页数：7

共 50 条

[41] THE SYNTHESIS OF 5-SUBSTITUTED 2,3-DIHYDROBENZOFURANS
ALBASTER, RJ
COTTRELL, IF
MARLEY, H
WRIGHT, SHB
SYNTHESIS-STUTTGART, 1988, (12): : 950 - 952
[42] SYNTHESIS AND STEREOCHEMISTRY OF 5-SUBSTITUTED 2-METHYLCYCLOHEPTANONES
MARSHALL, JA
PARTRIDGE, JJ
JOURNAL OF ORGANIC CHEMISTRY, 1968, 33 (11): : 4090 - +
[43] STEREOSELECTIVE SYNTHESIS OF ANOMERS OF 5-SUBSTITUTED 2'-DEOXYURIDINES
AOYAMA, H
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1987, 60 (06) : 2073 - 2077
[44] FACILE SYNTHESIS OF 5-SUBSTITUTED 2-ACETYLTHIOPHENES
GODA, H
SATO, M
IHARA, H
HIRAYAMA, C
SYNTHESIS-STUTTGART, 1992, (09): : 849 - 851
[45] Photochemical synthesis of N-substituted 3-hydroxy-2-pyrrolidinones
Obkircher, M
Seufert, W
Giese, B
SYNLETT, 2005, (07) : 1182 - 1184
[46] A Versatile Organozinc Approach to the Synthesis of Potential Organic Functional Building Blocks: 5-Substituted 3-Bromo-2-Methylthiophene Derivatives
Cheon, Jong-Woo
Cho, Hyun-Hee
Kim, Seung-Hoi
BULLETIN OF THE KOREAN CHEMICAL SOCIETY, 2015, 36 (04) : 1266 - 1269
[47] Synthesis of 5-substituted resorcinol derivatives via cross-coupling reactions
Dol, GC
Kamer, PCJ
van Leeuwen, PWNM
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 1998, 1998 (02) : 359 - 364
[48] A NEW APPROACH TO THE SYNTHESIS OF N-PROTECTED 2-SUBSTITUTED AND 5-SUBSTITUTED 3-HALOPYRROLES
MASQUELIN, T
OBRECHT, D
SYNTHESIS-STUTTGART, 1995, (03): : 276 - 284
[49] Efficient Synthesis of 4-and 5-Substituted 2-Aminopyrimidines by Coupling of β-Chlorovinyl Aldehydes and Guanidines
Komendantova, Anna S.
Komkov, Alexander V.
Volkova, Yulia A.
Zavarzin, Igor V.
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2017, 2017 (29) : 4260 - 4264
[50] Stereoselective formation of chiral trans-4-hydroxy-5-substituted 2-pyrrolidinones: syntheses of streptopyrrolidine and 3-epi-epohelmin A
Si, Chang-Mei
Mao, Zhuo-Ya
Liu, Yi-Wen
Du, Zhen-Ting
Wei, Bang-Guo
Lin, Guo-Qiang
ORGANIC CHEMISTRY FRONTIERS, 2015, 2 (11): : 1485 - 1499

← 1 2 3 4 5 →