[2+2] Cycloaddition reactions of imines with cyclic ketenes:: Synthesis of 1,3-thiazolidine derived spiro-β-lactams and their transformations

被引：14
|
作者：
Cremonesi, G
Dalla Croce, P
La Rosa, C
机构：
[1] Ist Chim Organ A Marchesini, Fac Farm, I-20133 Milan, Italy
[2] CNR, ISTM, Dipartimento Chim Organ & Ind, I-20133 Milan, Italy
来源：
HELVETICA CHIMICA ACTA | 2005年 / 88卷 / 06期
关键词：
D O I：
10.1002/hlca.200590125
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Unsymmetric cyclic ketenes were generated from N-acyl-1,3-thiazolidine-2-carboxylic acids la-c by means of Mukaiyama's reagent, and then reacted with imines 2a - c to the new, isomeric spiro-beta-lactams 3 and 4 via [2+2] cycloaddition (Staudinger ketene-imine reaction; Scheme 1). The reactions were stereoselective (Table 1) and mainly afforded the spiro-beta-lactams with a relative trans configuration. The spiro-beta-lactams could be transformed into the corresponding monocyclic beta-lactams by means of thiazolidine ring opening or into substituted thiazolidines via hydrolysis of the beta-lactam ring.
引用
收藏
页码：1580 / 1588
页数：9
相关论文
共 50 条
  • [41] Cycloaddition chemistry of 1,3-dienes on the silicon(001) surface: Competition between [4+2] and [2+2] reactions
    Hovis, JS
    Liu, HB
    Hamers, RJ
    JOURNAL OF PHYSICAL CHEMISTRY B, 1998, 102 (35): : 6873 - 6879
  • [42] Synthesis and (3+2) cycloaddition reactions of N,N E1 and C,N-cyclic azomethine imines
    Belskaya, Nataliya P.
    Bakulev, Vasiliy A.
    Fan, Zhijin
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2016, 52 (09) : 627 - 636
  • [43] Access to Spiro Bis-β-lactams via a Metal-Free Microwave-Assisted Wolff Rearrangement/Staudinger [2+2] Cycloaddition Cascade Involving 3-Diazotetramic Acids and Imines
    Krivovicheva, Vasilisa
    Lyutin, Ivan
    Kantin, Grigory
    Dar'in, Dmitry
    JOURNAL OF ORGANIC CHEMISTRY, 2024, 89 (05): : 3585 - 3589
  • [44] Rh2(OAc)4 catalyzed substrate selective [4+2]/[2+2] cycloaddition of acylketenes: a highly chemo- and regioselective synthesis of spiro(oxindolyl)oxazinones and β-lactams
    Reddy, B. V. Subba
    Karthik, Govindaraju
    Rajasekaran, Tamilselvan
    Antony, Aneesh
    Sridhar, B.
    TETRAHEDRON LETTERS, 2012, 53 (19) : 2396 - 2401
  • [45] Tandem [2+2] cycloaddition and Cope rearrangement in reactions of cross-conjugated azatrienes with conjugated ketenes: a facile single step synthesis of novel azocinone derivatives
    Singh, Parvesh
    Bhargava, Gaurav
    Mahajan, Mohinder P.
    TETRAHEDRON, 2006, 62 (48) : 11267 - 11273
  • [46] STEREOCHEMICAL FEATURES OF THE (2+2) CYCLOADDITION REACTIONS OF CHIRAL ALLENES .1. THE CYCLOADDITION OF ENANTIOENRICHED 1,3-DIMETHYLALLENE WITH THE MONOSUBSTITUTED ALKENES ACRYLONITRILE AND METHYL ACRYLATE
    PASTO, DJ
    SUGI, KD
    JOURNAL OF ORGANIC CHEMISTRY, 1991, 56 (12): : 3795 - 3801
  • [47] A ONE-STEP SYNTHESIS OF 2,3-DIHYDRO-1,4-BENZOTHIAZINES AND PHENOTHIAZINES FROM 1,3-THIAZOLIDINE DERIVATIVES OF CYCLOHEXANONES
    CAPUTO, R
    FERRERI, C
    LONGOBARDO, L
    MASTROIANNI, D
    PALUMBO, G
    PEDATELLA, S
    HETEROCYCLES, 1993, 36 (07) : 1641 - 1644
  • [48] Synthesis of spiro[pyrrolo[2,1-b][1,3]benzothiazole-3,2′-[1,3]thiazolo[3,2-a]pyrimidine] via cycloaddition reactions
    Zeng, Qing
    Ren, Demin
    Fu, Xingliang
    Li, Xiaofang
    JOURNAL OF CHEMICAL RESEARCH, 2018, (05) : 260 - 263
  • [49] Synthesis of novel spiro-[3H-indole-3,3′-[1,2,4]triazolidine]-2-ones via azomethine imines
    Azizian, J
    Morady, AV
    Soozangarzadeh, S
    Asadi, A
    TETRAHEDRON LETTERS, 2002, 43 (52) : 9721 - 9723
  • [50] 1,3-DIPOLAR CYCLOADDITION REACTIONS OF NITRILE OXIDES AND NITRILE IMINES WITH 2-METHOXYVINYL PHENYL KETONE
    COUTOULIARGYROPOULOU, E
    THESSALONIKEOS, E
    JOURNAL OF HETEROCYCLIC CHEMISTRY, 1991, 28 (02) : 429 - 432
12345