1,7-Diazaspiro[5.5]undecane - A Neglected Heterocycle

被引：7

作者：

Cordes, Jens ^{[1
]}

Murray, Philip R. D. ^{[1
]}

White, Andrew J. P. ^{[1
]}

Barrett, Anthony G. M. ^{[1
]}

机构：

[1] Univ London Imperial Coll Sci Technol & Med, Dept Chem, London SW7 2AZ, England

来源：

ORGANIC LETTERS | 2013年 / 15卷 / 19期

基金：

欧洲研究理事会;

关键词：

D O I：

10.1021/ol402301g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A convenient and simple three step synthesis of 1,7-diazaspiro[5.5]undecane via Claisen condensation and acid catalyzed decarboxylation and spirocyclization of N-Boc-delta-valerolactam is described. Reactions of this spiroaminal with electrophiles including alkyl halides, alkane dihalides, acid chlorides, and sulfonyl chlorides gave either spirocyclic adducts or tetrahydropyridine derivatives. Additionally, the parent heterocycle is a novel bidentate ligand and formed complexes with ruthenium(II) and copper(II).

引用

页码：4992 / 4995

页数：4

共 16 条

[11] An approach to the isoschizozygane alkaloid core using a 1,4-dipolar cycloaddition of a cross-conjugated heteroaromatic betaine [J].

Padwa, A ;

Flick, AC ;

Lee, HI .

ORGANIC LETTERS, 2005, 7 (14) :2925-2928

[12]

Pawlenko S., 1992, HOUBEN WEYL METHODS, P545

[13] AMINO-ACIDS AND PEPTIDES .110. INFRARED-SPECTRA OF POLYCYCLIC SPIRO-DILACTAMS WITH NON-PLANAR AMIDE BONDS [J].

SMOLIKOVA, J ;

KOBLICOVA, Z ;

BLAHA, K .

COLLECTION OF CZECHOSLOVAK CHEMICAL COMMUNICATIONS, 1973, 38 (02) :532-547

[14] An efficient synthesis of an αvβ3 antagonist [J].

Yasuda, N ;

Hsiao, Y ;

Jensen, MS ;

Rivera, NR ;

Yang, CH ;

Wells, KM ;

Yau, J ;

Palucki, M ;

Tan, LS ;

Dormer, PG ;

Volante, RP ;

Hughes, DL ;

Reider, PJ .

JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (06) :1959-1966

[15]

Ziegler T., 2005, SCI SYNTH, V21, P43

[16] CATALYTIC-HYDROGENATION OF ANIMALS [J].

ZONDLER, H ;

PFLEIDERER, W .

HELVETICA CHIMICA ACTA, 1975, 58 (08) :2247-2260

← 1 2 →