2-(ethoxycarbonylmethyl)-1H-naphtho[1,8-de]-1,2,3-triazine anion:: a new glycine enolate equivalent

被引：1

作者：

Anilkumar, R ^{[1
]}

Chandrasekhar, S ^{[1
]}

Sridhar, M ^{[1
]}

机构：

[1] Indian Inst Sci, Dept Organ Chem, Bangalore 560012, Karnataka, India

来源：

TETRAHEDRON LETTERS | 2000年 / 41卷 / 34期

关键词：

amino acid; glycine enolate; naphthotriazine;

D O I：

10.1016/S0040-4039(00)01115-1

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The titled triazine can be alkylated with LDA and a variety of alkyl halides: subsequent reduction with aluminium amalgam cleaves the naphthotriazine moiety to afford substituted alpha amino acids in excellent overall yields; the sequence defines a novel methodology that can be applied under non-acidic and largely non-aqueous conditions. (C) 2000 Elsevier Science Ltd. All rights reserved.

引用

页码：6665 / 6668

页数：4

共 50 条

[1] An α-aminomethyl carbanion equivalent via a novel Barbier reaction:: (1H-naphtho[1,8-de]-1,2,3-triazin-2-yl)methyl anion
Chandrasekhar, S
Sridhar, M
TETRAHEDRON LETTERS, 2000, 41 (23) : 4685 - 4688
[2] Synthesis and reductive cleavage of 2-alkyl-1H-naphtho [1,8-de]-1,2,3-triazine: A chirally viable alternative to the Gabriel amine synthesis
Chandrasekhar, Sosale
Sridhar, Malayalam
Journal of the Indian Institute of Science, 2001, 81 (02) : 155 - 158
[3] THE STRUCTURE OF "2-METHYL-2H-NAPHTHO[1,8-DE]TRIAZINE
HAZELL, A
MARIEZCURRENA, R
ACTA CRYSTALLOGRAPHICA SECTION B-STRUCTURAL SCIENCE, 1980, 36 (DEC): : 3140 - 3142
[4] 1,2,3-TRIAZINE
OHSAWA, A
ARAI, H
OHNISHI, H
IGETA, H
JOURNAL OF THE CHEMICAL SOCIETY-CHEMICAL COMMUNICATIONS, 1981, (22) : 1174 - 1174
[5] 2-(4-Chlorophenyl)naphtho[1,8-de][1,3,2]diazaborinane
Akerman, Matthew P.
Robinson, Ross S.
Slabber, Cathryn A.
ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2011, 67 : O1873 - U1520
[6] SYNTHESES AND PROPERTIES OF 2,2'-BINAPHTHO[1,8-DE]-1,3-DITHIINYLIDENE AND ITS SELENIUM ANALOG, 2-(1,3-DITHIOL-2-YLIDENE)NAPHTHO[1,8-DE]-1,3-DITHIIN, AND 2-(4H-THIOPYRAN-4-YLIDENE)NAPHTHO[1,8-DE]-1,3-DITHIIN
YUI, K
ASO, Y
OTSUBO, T
OGURA, F
BULLETIN OF THE CHEMICAL SOCIETY OF JAPAN, 1988, 61 (03) : 953 - 959
[7] Synthesis of 1,2,3-Triazine Derivatives by Deoxygenation of 1,2,3-Triazine 1-Oxides
Rivera, Gildardo
De Angelis, Luca
Al-Sayyed, Ammar
Biswas, Soumen
Arman, Hadi
Doyle, Michael P.
ORGANIC LETTERS, 2022, 24 (36) : 6543 - 6547
[8] REACTIVE INTERMEDIATES .4. AMINATION OF NAPHTHO[1,8-DE]-TRIAZINE
REES, CW
STORR, RC
JOURNAL OF THE CHEMICAL SOCIETY C-ORGANIC, 1969, (05): : 756 - &
[9] A NOVEL RING FISSION OF A 1,3-DIMETHYL-1H-NAPHTHO[1,8-DE]-1,2,3-TRIAZINIUM SALT
BEECKEN, H
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 1967, 6 (04) : 360 - &
[10] 2-[4-(Methylsulfanyl)phenyl]naphtho[1,8-de][1,3,2]diazaborinane
Slabber, Cathryn A.
Akerman, Matthew P.
Robinson, Ross S.
ACTA CRYSTALLOGRAPHICA SECTION E-STRUCTURE REPORTS ONLINE, 2011, 67 : O1338 - U2134

← 1 2 3 4 5 →