The efficient, enantioselective synthesis of quinoxaline, pyrazine and 1,2,4-triazine substituted α-amino acids from vicinal tricarbonyls

被引：27

作者：

Adlington, RM ^{[1
]}

Baldwin, JE ^{[1
]}

Catterick, D ^{[1
]}

Pritchard, GJ ^{[1
]}

机构：

[1] Univ Oxford, Dyson Perrins Lab, Oxford OX1 3QY, England

来源：

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1 | 2001年 / 07期

关键词：

D O I：

10.1039/b010134f

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The reaction of diamines and amidrazones with alpha -amino acid vicinal tricarbonyls has been shown to be a versatile route towards novel heterocyclic alpha -amino acids. This route is also applicable to parallel synthesis and has allowed the formation of a range of heterocyclic amino acid systems.

引用

页码：668 / 679

页数：12

共 42 条

[1] A versatile synthetic route to quinoxaline, pyrazine and 1,2,4-triazine substituted α-amino acids from vicinal tricarbonyls [J].

Adlington, RM ;

Baldwin, JE ;

Catterick, D ;

Pritchard, GJ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (03) :299-302

[2] The synthesis of novel heterocyclic substituted α-amino acids;: further exploitation of α-amino acid alkynyl ketones as reactive substrates [J].

Adlington, RM ;

Baldwin, JE ;

Catterick, D ;

Pritchard, GJ ;

Tang, LT .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (15) :2311-2316

[3] The synthesis of novel heterocyclic substituted α-amino acids;: further exploitation of α-amino acid alkynyl ketones [J].

Adlington, RM ;

Baldwin, JE ;

Catterick, D ;

Pritchard, GJ ;

Tang, LT .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 2000, (03) :303-305

[4] A versatile approach to pyrimidin-4-yl substituted alpha-amino acids from alkynyl ketones; the total synthesis of L-lathyrine [J].

Adlington, RM ;

Baldwin, JE ;

Catterick, D ;

Pritchard, GJ .

CHEMICAL COMMUNICATIONS, 1997, (18) :1757-1758

[5] The synthesis of pyrimidin-4-yl substituted α-amino acids.: A versatile approach from alkynyl ketones [J].

Adlington, RM ;

Baldwin, JE ;

Catterick, D ;

Pritchard, GJ .

JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1999, (08) :855-866

[6] AN EFFICIENT AND MILD SYNTHESIS OF HIGHLY SUBSTITUTED IMIDAZOLES [J].

BRACKEEN, MF ;

STAFFORD, JA ;

FELDMAN, PL ;

KARANEWSKY, DS .

TETRAHEDRON LETTERS, 1994, 35 (11) :1635-1638

[7]

Cheeseman G.W.H., 1972, Adv. Heterocycl. Chem, V14, P99, DOI [10.1016/S0065-2725(08)60953-8, DOI 10.1016/S0065-2725(08)60953-8]

[8] A concise synthesis of either enantiomer of azatyrosine [J].

Cooper, MS ;

Seton, AW ;

Stevens, AW ;

Stevens, MFG ;

Westwell, AD .

BIOORGANIC & MEDICINAL CHEMISTRY LETTERS, 1996, 6 (21) :2613-2616

[9] ALPHA-METHOXY-ALPHA-TRIFLUOROMETHYLPHENYLACETIC ACID, A VERSATILE REAGENT FOR DETERMINATION OF ENANTIOMERIC COMPOSITION OF ALCOHOLS AND AMINES [J].

DALE, JA ;

DULL, DL ;

MOSHER, HS .

JOURNAL OF ORGANIC CHEMISTRY, 1969, 34 (09) :2543-&

[10] RECENT DEVELOPMENTS IN THE STEREOSELECTIVE SYNTHESIS OF ALPHA-AMINO-ACIDS [J].

DUTHALER, RO .

TETRAHEDRON, 1994, 50 (06) :1539-1650

← 1 2 3 4 5 →