Functionalization of dipyrromethanes via hetero-Diels-Alder reaction with azo- and nitrosoalkenes

被引：19
|
作者：
Pereira, Nelson A. M. [1 ]
Lemos, Americo [2 ]
Serra, Armenio C. [1 ]
Pinho e Melo, Teresa M. V. D. [1 ]
机构：
[1] Univ Coimbra, Dept Chem, P-3004535 Coimbra, Portugal
[2] Univ Algarve, FCT, CIQA, P-8005139 Faro, Portugal
来源：
TETRAHEDRON LETTERS | 2013年 / 54卷 / 12期
关键词：
Dipyrromethanes; Azoalkenes; Nitrosoalkenes; Hetero-Diels-Alder reaction; BODIPY DYES; CYCLOADDITION REACTIONS; BORON-DIPYRROMETHENE; DERIVATIVES; PORPHYRINS; CHEMISTRY; RECEPTORS;
D O I：
10.1016/j.tetlet.2013.01.032
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
5,5'-Diethyl- and 5-phenyldipyrromethanes participate in cycloadditions with azo- and nitrosoalkenes giving dipyrromethanes with side chains containing open chain oximes and hydrazones. By controlling reaction stoichiometry it is possible to get mono or 1,9-disubstituted derivatives. The reported methodology gave access to a range of dipyrromethanes with good structural features for various applications. It was demonstrated that reduction of dipyrromethanes containing alpha-oximino ester groups opens the way to new alpha-amino esters. (c) 2013 Elsevier Ltd. All rights reserved.
引用
收藏
页码：1553 / 1557
页数：5
相关论文
共 50 条
  • [1] On-Water Synthesis of Dipyrromethanes via Bis-Hetero-Diels-Alder Reaction of Azo- and Nitrosoalkenes with Pyrrole
    Pereira, Nelson A. M.
    Lopes, Susana M. M.
    Lemos, Americo
    Pinho e Melo, Teresa M. V. D.
    SYNLETT, 2014, 25 (03) : 423 - 427
  • [2] DIACETONEGLUCOSE AS AUXILIARY GROUP FOR THE ASYMMETRIC HETERO-DIELS-ALDER REACTION WITH NITROSOALKENES
    ARNOLD, T
    ORSCHEL, B
    REISSIG, HU
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION IN ENGLISH, 1992, 31 (08): : 1033 - 1035
  • [3] Asymmetric functionalization of benzenes via an organocatalytic hetero-Diels-Alder reaction
    Ali, Shaukat
    Israr, Muhammad
    CHEMICAL COMMUNICATIONS, 2022, 58 (71) : 9851 - 9854
  • [4] Hetero-Diels-Alder Reactions of α-Nitrosoalkenes with Ferrocenyl, Hetaryl and Cycloaliphatic Thioketones
    Mloston, Grzegorz
    Urbaniak, Katarzyna
    Zimmer, Reinhold
    Reissig, Hans-Ulrich
    Heimgartner, Heinz
    CHEMISTRYSELECT, 2018, 3 (42): : 11724 - 11728
  • [5] SYNTHESIS OF AZAANTHRAQUINONE DERIVATIVES VIA A HETERO-DIELS-ALDER REACTION
    NEBOIS, P
    BARRET, R
    FILLION, H
    TETRAHEDRON LETTERS, 1990, 31 (18) : 2569 - 2572
  • [6] INTRAMOLECULAR AND INTERMOLECULAR HETERO-DIELS-ALDER REACTION .12. HETERO-DIELS-ALDER REACTION OF ENAMINECARBALDEHYDES - AN ENTRY TO BRANCHED AMINOSUGARS
    TIETZE, LF
    VOSS, E
    HARMS, K
    SHELDRICK, GM
    TETRAHEDRON LETTERS, 1985, 26 (43) : 5273 - 5276
  • [7] Facile Synthesis of Furowarfarins via Hetero-Diels-Alder Cycloaddition Reaction
    Soman, Shubhangi S.
    Patel, Jagdish M.
    SYNTHETIC COMMUNICATIONS, 2013, 43 (06) : 775 - 783
  • [8] SYNTHESIS OF (+/-)-RAMULOSIN VIA INVERSE TYPE HETERO-DIELS-ALDER REACTION
    VOGT, K
    SCHMIDT, RR
    TETRAHEDRON, 1988, 44 (11) : 3271 - 3280
  • [9] Total Synthesis of (+)-Cytosporolide A via a Biomimetic Hetero-Diels-Alder Reaction
    Takao, Ken-ichi
    Noguchi, Shuji
    Sakamoto, Shu
    Kimura, Mizuki
    Yoshida, Keisuke
    Tadano, Kin-ichi
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2015, 137 (50) : 15971 - 15977
  • [10] Catalytic enantioselective hetero-Diels-Alder reactions of an azo compound
    Kawasaki, Masanori
    Yamamoto, Hisashi
    Journal of the American Chemical Society, 2006, 128 (51): : 16482 - 16483
12345