Newer Developments in the Synthesis of P-Heterocycles

被引:15
作者
Keglevich, Gyoergy [1 ]
机构
[1] Budapest Univ Technol & Econ, Dept Organ Chem & Technol, H-1521 Budapest, Hungary
关键词
P-heterocycles; 3-phospholene; 1-oxides; phospholane oxides; hexahydrophosphinine oxides; 7-phosphanorbornene; 7-oxides; phosphinic derivatives; phosphine boranes; phosphines; TERTIARY PHOSPHINE OXIDES; MICROWAVE-ASSISTED ESTERIFICATION; WITTIG REACTION; MITSUNOBU REACTIONS; ORGANIC-SYNTHESIS; ZU PHOSPHINEN; IONIC LIQUID; ACID; HYDROLYSIS; REDUCTION;
D O I
10.2174/1385272823666190726093322
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The P-heterocyclic field forms a special part of organophosphorus chemistry, and is a special discipline within heterocyclic chemistry. The relevant results accumulated in the group of the author of this minireview in last 5 years are summarized. After surveying the conformational situation of cyclic phosphinates, their Microwave (MW)-assisted direct esterification and the T3P (R)-promoted esterification are discussed. The next chapters describe newer results regarding the interpretation and modelling of the rate enhancing effect of MWs, and on an important, but somewhat neglected field, the hydrolysis of phosphinates. New results on the ring enlargement of 5-membered unsaturated P-heterocycles to 6-ring species, as well as on the synthesis of 7-phosphanorbornene derivatives, and their refunctionalization are also included. Novel findings on the preparation of cyclic amides and imides are also explored. Last but not least, the user-friendly deoxygenations of cyclic phosphine oxides elaborated by us are shown. The reader will be able to discover green chemical considerations and accomplishments throughout the series of organophosphorus transformations reviewed.
引用
收藏
页码:1342 / 1355
页数:14
相关论文
共 104 条
[1]   Organophosphorus-catalyzed diaza-Wittig reaction: application to the synthesis of pyridazines [J].
Abed, Hassen Bel ;
Mammoliti, Oscar ;
Bande, Omprakash ;
Van Lommen, Guy ;
Herdewijn, Piet .
ORGANIC & BIOMOLECULAR CHEMISTRY, 2014, 12 (36) :7159-7166
[2]   A Theoretical Study on the Conformation of 5-and 6-Membered P-Heterocycles: 1-Substituted 2,3,4,5-Tetrahydro-1H-Phosphole 1-Oxides and 1,2,3,4,5,6-Hexahydrophosphinine 1-Oxides [J].
Abranyi-Balogh, Peter ;
Keglevich, Gyorgy .
CURRENT ORGANIC CHEMISTRY, 2017, 21 (21) :2216-2228
[3]   Theoretical Calculations on the Mechanism of the T3P®-Promoted Esterification and Amidation of Phosphinic Acids [J].
Abranyi-Balogh, Peter ;
Jablonkai, Erzsebet ;
Henyecz, Reka ;
Milen, Matyas ;
Keglevich, Gyoergy .
CURRENT ORGANIC CHEMISTRY, 2016, 20 (10) :1135-1142
[4]  
Amitrano R, 2009, PEPTIDES YOUTH ADV E
[5]  
[Anonymous], 2000, A Guide to Organophosphorus Chemistry
[6]   Alkylating Esterification of 1-Hydroxy-3-phospholene Oxides under Solventless MW Conditions [J].
Balint, Erika ;
Jablonkai, Erzsebet ;
Balint, Maria ;
Keglevich, Gyoergy .
HETEROATOM CHEMISTRY, 2010, 21 (04) :211-214
[7]   Propanephosphonic Acid Anhydride (T3P®) - A Benign Reagent for Diverse Applications Inclusive of Large-Scale Synthesis [J].
Basavaprabhu ;
Vishwanatha, T. M. ;
Panguluri, Nageswara Rao ;
Sureshbabu, Vommina V. .
SYNTHESIS-STUTTGART, 2013, 45 (12) :1569-1601
[8]  
Buckley B.R., 2005, COMPREHENSIVE ORGANI, V5, P127, DOI [10.1016/B0-08-044655-8/00093-3, DOI 10.1016/B0-08-044655-8/00093-3]
[9]   Mitsunobu Reactions Catalytic in Phosphine and a Fully Catalytic System [J].
Buonomo, Joseph A. ;
Aldrich, Courtney C. .
ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2015, 54 (44) :13041-13044
[10]   THE QUEST FOR CARBANION-PROMOTED DISSOCIATIVE PATHWAYS IN THE HYDROLYSIS OF ARYL PHOSPHINATES [J].
CEVASCO, G ;
THEA, S .
JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 2, 1993, (06) :1103-1106