Synthesis of N-substituted 3-aminomethylidenetetramic acids

被引：28

作者：

Pirc, S ^{[1
]}

Bevk, D ^{[1
]}

Jakse, R ^{[1
]}

Recnik, S ^{[1
]}

Golic, L ^{[1
]}

Golobic, A ^{[1
]}

Meden, A ^{[1
]}

Stanovnik, B ^{[1
]}

Svete, J ^{[1
]}

机构：

[1] Univ Ljubljana, Fac Chem & Chem Technol, Ljubljana 1000, Slovenia

来源：

SYNTHESIS-STUTTGART | 2005年 / 17期

关键词：

amines; chiral pool; coupling; heterocycles; enaminones;

D O I：

10.1055/s-2005-916072

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

(S)-3-(Dimethylamino)methylidene-5-benzyltetramic acid derivatives 4a and 4b were prepared in three steps from N-protected (S)-3-phenylaianines la and 1b, respectively. Similarly, N-[N-(benzyloxycarbonyl)glycyl]glycine (1c) was transformed into the enaminone 4c. Acid-catalysed coupling of enaminones 4a-c with aliphatic, aromatic, and heteroaromatic primary amines 5-34 afforded the corresponding N(Y)-substituted 3-aminomethylidene-tetramic acid derivatives 35-64 in 29-96% yields.

引用

页码：2969 / 2988

页数：20

共 50 条

[1] SYNTHESIS OF N-SUBSTITUTED AMINOSULFONIC ACIDS
ZEID, I
ISMAIL, I
[J]. CHEMISTRY & INDUSTRY, 1973, (08) : 380 - 380
[2] SYNTHESIS OF N-SUBSTITUTED AMINOSULFONIC ACIDS
ZEID, I
ISMAIL, I
HELFERIC.B
[J]. ANNALEN DER CHEMIE-JUSTUS LIEBIG, 1972, 761 (JUL): : 118 - &
[3] SYNTHESIS OF N-SUBSTITUTED AMINO SULFONIC ACIDS .3.
ZEID, I
MOUSSA, H
ISMAIL, I
[J]. ANNALEN DER CHEMIE-JUSTUS LIEBIG, 1974, (11): : 1816 - 1819
[4] SYNTHESIS OF CYCLOALKYLHYDROXAMIC ACIDS AND THEIR N-SUBSTITUTED DERIVATIVES
ALJALLO, HN
AHMED, SS
SALEH, FI
ABBAS, FM
[J]. JOURNAL OF CHEMICAL AND ENGINEERING DATA, 1981, 26 (03): : 338 - 340
[5] EFFICIENT SYNTHESIS OF N-SUBSTITUTED ARYLGLYOXYLOHYDROXAMIC ACIDS
BURCHARDT, A
GEFFKEN, D
[J]. ARCHIV DER PHARMAZIE, 1988, 321 (05) : 311 - 312
[6] SYNTHESIS OF N-SUBSTITUTED AMIDES OF UNSATURATED ACIDS
FARAFONTOVA, VI
PODGORNOVA, VA
USTAVSHCHIKOV, VF
[J]. JOURNAL OF APPLIED CHEMISTRY OF THE USSR, 1975, 48 (01): : 239 - 242
[7] SYNTHESIS OF N-SUBSTITUTED 2-AMINOETHANETHIOSULFURIC ACIDS
KLAYMAN, DL
GILMORE, WF
[J]. JOURNAL OF MEDICINAL CHEMISTRY, 1964, 7 (06) : 823 - &
[8] A NOVEL SYNTHESIS OF N-SUBSTITUTED AMINO-ACIDS
NAIM, SS
KHAN, NH
SIDDIQUI, AA
[J]. INDIAN JOURNAL OF CHEMISTRY SECTION B-ORGANIC CHEMISTRY INCLUDING MEDICINAL CHEMISTRY, 1980, 19 (07): : 622 - 624
[9] SYNTHESIS OF N-SUBSTITUTED AMIDES OF UNSATURATED-ACIDS
FARAFONTOVA, VI
PODGORNOVA, VA
USTAVSHCHIKOV, BF
[J]. JOURNAL OF APPLIED CHEMISTRY OF THE USSR, 1976, 49 (04): : 979 - 981
[10] SYNTHESIS OF N-SUBSTITUTED MALEAMIC ACIDS AS POTENTIAL HYPOCHOLESTEREMICS
LIU, KC
CHEN, TB
JAN, HJ
SHIH, CY
[J]. JOURNAL OF THE CHINESE CHEMICAL SOCIETY, 1973, 20 (03) : 163 - 169

← 1 2 3 4 5 →