THIO-CLAISEN REARRANGEMENT ON PYROGLUTAMATES

被引:10
作者
JAIN, S [1 ]
SINHA, N [1 ]
DIKSHIT, DK [1 ]
ANAND, N [1 ]
机构
[1] CENT DRUG RES INST, DIV MED CHEM, LUCKNOW 226001, UTTAR PRADESH, INDIA
关键词
D O I
10.1016/0040-4039(95)01731-V
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
S-allyl/propargyl/methallyl thioimminium salts derived from methyl 1-benzyl-5-thioxoprolinate (1) undergoes a facile thio-Claisen rearrangement which provides an easy access to 4-substituted thioxoprolinates (2-4).
引用
收藏
页码:8467 / 8468
页数:2
相关论文
共 14 条
[1]   AMINO-ACID SYNTHESIS USING (L)-PYROGLUTAMIC ACID AS A CHIRAL STARTING MATERIAL [J].
BALDWIN, JE ;
MIRANDA, T ;
MOLONEY, M ;
HOKELEK, T .
TETRAHEDRON, 1989, 45 (23) :7459-7468
[2]   A SIMPLE ASYMMETRIC-SYNTHESIS OF 2-SUBSTITUTED PYRROLIDINES AND 5-SUBSTITUTED PYRROLIDINONES [J].
BURGESS, LE ;
MEYERS, AI .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (06) :1656-1662
[3]   ALDOL REACTIONS OF PYROGLUTAMATES - CHIRAL SYNTHESIS OF 4-ALPHA(S)-(ARYLMETHYL)PYROGLUTAMATES AND 4-BETA(R)-(ARYLMETHYL)PYROGLUTAMATES [J].
DIKSHIT, DK ;
PANDAY, SK .
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (06) :1920-1924
[4]   REGIOSELECTIVE NUCLEOPHILIC-ATTACK ON N-BOC-PYROGLUTAMATE ETHYL-ESTER [J].
EZQUERRA, J ;
DEMENDOZA, J ;
PEDREGAL, C ;
RAMIREZ, C .
TETRAHEDRON LETTERS, 1992, 33 (38) :5589-5590
[5]   STEREOSELECTIVE REACTIONS OF LITHIUM ENOLATES DERIVED FROM N-BOC PROTECTED PYROGLUTAMIC ESTERS [J].
EZQUERRA, J ;
PEDREGAL, C ;
RUBIO, A ;
YRURETAGOYENA, B ;
ESCRIBANO, A ;
SANCHEZFERRANDO, F .
TETRAHEDRON, 1993, 49 (38) :8665-8678
[6]   TOTAL SYNTHESIS OF THE ANGIOTENSIN-CONVERTING ENZYME INHIBITOR-A58365A - ON THE USE OF PYROGLUTAMATE AS A CHIRAL EDUCT [J].
FANG, FG ;
DANISHEFSKY, SJ .
TETRAHEDRON LETTERS, 1989, 30 (28) :3621-3624
[7]   SIMPLE ANALOGS OF ACROMELIC ACID, WHICH ARE HIGHLY-ACTIVE AGONISTS OF KAINATE TYPE NEUROEXCITANT [J].
HASHIMOTO, K ;
HORIKAWA, M ;
SHIRAHAMA, H .
TETRAHEDRON LETTERS, 1990, 31 (48) :7047-7050
[8]   SYNTHESIS, CHEMICAL-PROPERTY, AND CYTOTOXICITY OF THE CARZINOPHILIN CONGENERS CARRYING A 2-(1-ACYLAMINO-1-ALKOXYCARBONYL)METHYLIDENE-1-AZABICYCLO[3.1.0]HEXANE SYSTEM [J].
HASHIMOTO, M ;
MATSUMOTO, M ;
YAMADA, K ;
TERASHIMA, S .
TETRAHEDRON LETTERS, 1994, 35 (14) :2207-2210
[9]   LACTAM ACETALS .24. REACTION WITH ACTIVATED HALOALKYL COMPOUNDS WITH AND WITHOUT ZINC [J].
JAIN, S ;
JAIN, R ;
SINGH, J ;
ANAND, N .
TETRAHEDRON LETTERS, 1994, 35 (18) :2951-2954
[10]   LACTAM AND AMIDE ACETALS .21. USE OF PYROGLUTAMIC ACID AND PROLINE IN CHIRAL SYNTHESIS OF CONFORMATIONALLY CONSTRAINED PIPERAZINONES [J].
JAIN, S ;
SUJATHA, K ;
KRISHNA, KVR ;
ROY, R ;
SINGH, J ;
ANAND, N .
TETRAHEDRON, 1992, 48 (23) :4985-4998