Entry to nitrogen-containing heterocycles by based-promoted heterocyclization on allenylamides of L-α-aminoacids

被引：28

作者：

Broggini, Gianluigi ^{[1
]}

Galli, Simona ^{[1
]}

Rigamonti, Micol ^{[1
]}

Sottocornola, Silvia ^{[1
]}

Zecchi, Gaetano ^{[1
]}

机构：

[1] Univ Insubria, Dipartimento Sci Chim & Ambientali, I-22100 Como, Italy

来源：

TETRAHEDRON LETTERS | 2009年 / 50卷 / 13期

关键词：

Allenes; Heterocyclization; Hydroamination; Microwave irradiation; Imidazolidinones; Pyrazinones; Pyrroles; ENDO-MODE CYCLIZATION; 1,3-DIPOLAR CYCLOADDITIONS; PYRROLE DERIVATIVES; ALLENES; BROMOALLENES; CARBOCYCLES; SULFOXIDES; OXACYCLES; ABSENCE;

D O I：

10.1016/j.tetlet.2009.01.074

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

Allenylamides of Boc-protected alpha-aminoacids easily gave in basic medium heterocyclic products arising from attack of the NH group on the inside C-C double bond of the 1,2-diene moiety, namely imidazolidinones, pyrazinones, and a pyrrole compound. The microwave-assisted heterocyclization occurred cleanly at C-beta of the allenyl group with formation of pyrazin-2-ones having an endo- or exocyclic double bond. (C) 2009 Elsevier Ltd. All rights reserved.

引用

页码：1447 / 1449

页数：3

共 31 条

[21] Construction of azacycles based on endo-mode cyclization of allenes
Mukai, C
Kobayashi, M
Kubota, S
Takahashi, Y
Kitagaki, S
[J]. JOURNAL OF ORGANIC CHEMISTRY, 2004, 69 (06) : 2128 - 2136
[22] A new entry to carbocycles:: synthesis of cyclopentene and cyclohexene derivatives through endo-mode ring closure of allenyl sulfones
Mukai, C
Ukon, R
Kuroda, N
[J]. TETRAHEDRON LETTERS, 2003, 44 (08) : 1583 - 1586
[23] A new entry to oxacycles via base-catalyzed endo mode cyclization of allenyl sulfoxides and sulfones
Mukai, C
Yamashita, H
Hanaoka, M
[J]. ORGANIC LETTERS, 2001, 3 (21) : 3385 - 3387
[24] Potassium carbonate-promoted stereospecific 5-Endo-Trig cyclization of unactivated allenes in the absence of any transition metals
Ohno, H
Kadoh, Y
Fujii, N
Tanaka, T
[J]. ORGANIC LETTERS, 2006, 8 (05) : 947 - 950
[25] A highly cis-selective synthesis of 2-ethynylaziridines by intramolecular amination of chiral bromoallenes:: Improvement of stereoselectivity based on the computational investigation
Ohno, H
Ando, K
Hamaguchi, H
Takeoka, Y
Tanaka, T
[J]. JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2002, 124 (51) : 15255 - 15266
[26] CHEMISTRY OF ALLENE SULFOXIDES - A NEW METHODOLOGY FOR THE SYNTHESIS OF SPIROKETALS AND 1,5-DIOXADECALIN RING-SYSTEMS
PAIRAUDEAU, G
PARSONS, PJ
UNDERWOOD, JM
[J]. JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1987, (22) : 1718 - 1720
[27] ROCHET P, 1994, SYNTHESIS-STUTTGART, P795
[28] Schuster H.F., 1984, ALLENES ORGANIC SYNT
[29] WIDENHOEFER RA, 2006, PURE APPL CHEM, V78, P197
[30] A new approach to the synthesis of 2-vinylthiophenes and selenophenes; competition between free radical and anionic cycloaromatization of bridged di- and tetrapropargylic sulfides and selenides
Zafrani, Y
Cherkinsky, M
Gottlieb, HE
Braverman, S
[J]. TETRAHEDRON, 2003, 59 (15) : 2641 - 2649

← 1 2 3 4 →