2-IMINOOXETANE CHEMISTRY .4. SYNTHESIS OF BETA-SUBSTITUTED PROPIONAMIDES

被引：9

作者：

BARBARO, G ^{[1
]}

BATTAGLIA, A ^{[1
]}

GIORGIANNI, P ^{[1
]}

机构：

[1] CNR,IST COMPOSTI CARBONIO CONTENENTI ETREOATOMI,I-40129 BOLOGNA,ITALY

来源：

JOURNAL OF ORGANIC CHEMISTRY | 1994年 / 59卷 / 04期

关键词：

D O I：

10.1021/jo00083a036

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

beta-substituted propionamides (RCHXCR(1)R(2)CONHAr) were synthesized in high yields by addition of protic and aprotic Lewis acids (C6H5SO3H, CF3COOH, CH3COOH, HI, MgBr2, ZnI2, CH3OH, H2O,2,4,6-(NO2)(3)C6H2OH) to 2-iminooxetanes. Studies on the stereochemistry of the acid addition to unsymmetrically C3,C4-monosubstituted 2-iminooxetanes indicate that product distribution depends on the steric and electronic nature of the substitutents of the oxetane moiety as well as on the nucleophilicity of the conjugate base derived from the acid.

引用

页码：906 / 913

页数：8

共 50 条

[11] SYNTHESIS OF OPTICALLY ACTIVE BETA-SUBSTITUTED ADAMANTONES
SNATZKE, G
ECKHARDT, G
CHEMISCHE BERICHTE-RECUEIL, 1968, 101 (06): : 2010 - &
[12] SYNTHESIS OF BETA-SUBSTITUTED ALPHA-IODOCYCLOALKENONES
SHA, CK
HUANG, SJ
TETRAHEDRON LETTERS, 1995, 36 (38) : 6927 - 6928
[13] ENZYMIC-SYNTHESIS OF BETA-SUBSTITUTED ALANINES
MURAKOSH.I
KURAMOTO, H
HAGINIWA, J
FOWDEN, L
PHYTOCHEMISTRY, 1972, 11 (01) : 177 - &
[14] SYNTHESIS AND REACTIONS OF BETA-SUBSTITUTED ETHYL SULFATES
TOMALIA, DA
FALK, JC
JOURNAL OF HETEROCYCLIC CHEMISTRY, 1972, 9 (04) : 891 - &
[15] Stereoselective synthesis of erythro beta-substituted aspartates
Antolini, L
Bucciarelli, M
Caselli, E
Davoli, P
Forni, A
Moretti, I
Prati, F
Torre, G
JOURNAL OF ORGANIC CHEMISTRY, 1997, 62 (25): : 8784 - 8789
[16] ENANTIOSELECTIVE AND DIASTEREOSELECTIVE SYNTHESIS OF BETA-SUBSTITUTED CYCLOALKANECARBOXYLATES
FANG, CL
SUEMUNE, H
SAKAI, K
JOURNAL OF ORGANIC CHEMISTRY, 1992, 57 (15): : 4300 - 4303
[17] Synthesis and biological activity of beta-substituted tryptamines
Maiden, Kristen
Kidd, Jesse
Morgan, Jeremy
ABSTRACTS OF PAPERS OF THE AMERICAN CHEMICAL SOCIETY, 2016, 251
[18] SYNTHESIS OF BETA-SUBSTITUTED TETRAHYDROFURANS BY THE PRINS REACTION
TALIPOV, RF
MUSLUKHOV, RR
SAFAROV, IM
YAMANTAEV, FA
SAFAROV, MG
KHIMIYA GETEROTSIKLICHESKIKH SOEDINENII, 1995, (05): : 605 - 608
[19] BETA-SUBSTITUTED THIOPHENE DERIVATIVES .4. SYNTHESIS AND PHARMACOLOGICAL ACTIVITY OF BIS (BETA-THIENYL) AMINOALCOHOLS AND BIS (BETA--THIENYL) AMINOALKENES
ROBBA, M
DUVAL, D
CHIMICA THERAPEUTICA, 1973, 8 (01): : 22 - 31
[20] BETA-SUBSTITUTED ENAMINES .4. SUBSTITUTION REACTIONS OF 1,1,2-TRIAMINOETHENES
BOHME, H
HOVER, W
ANNALEN DER CHEMIE-JUSTUS LIEBIG, 1971, 748 (JUN): : 59 - &

← 1 2 3 4 5 →