Stereoselective synthesis of dihydrothiadiazinoazines and dihydrothiadiazinoazoles and their pyrolytic desulfurization ring contraction

被引：23
作者：
Al-Etaibi, Alya [2 ]
John, Elizabeth [1 ]
Ibrahim, Maher R. [1 ]
Al-Awadi, Nouria A. [1 ]
Ibrahim, Yehia A. [1 ]
机构：
[1] Kuwait Univ, Fac Sci, Dept Chem, Safat 13060, Kuwait
[2] Publ Author Appl Educ & Training, Coll Hlth Sci, Dept Nat Sci, Kuwait, Kuwait
来源：
TETRAHEDRON | 2011年 / 67卷 / 34期
关键词：
Pyrolysis; Stereoselective synthesis; 1,2,4]Triazolo[3,4-b][1,3,4]thiadiazines; 1,2,4]Triazino[3,4-b][1,3,4]thiadiazin-4-ones; 1,3,4]Thiadiazino[2,3-b]quinazolin-10-ones; Pyrazolo[5,1-b][1,2,4]triazoles; Pyrazolo[5,1-c][1,2,4]triazin-4-ones; Pyrazolo[4,3-b]quinazolin-9-ones; GAS-PHASE THERMOLYSIS; CARBONATE PYROLYSIS; INTERESTING ROUTES; SCHIFF-BASES; CYCLIZATION; SYSTEMS;
D O I：
10.1016/j.tet.2011.06.034
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
Intramolecular base catalyzed C-C bond formation led to exclusive stereoselective syntheses of trans-6,7-dihydro-5H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazines, trans-7,8-dihydro-6H-[1,2,4]triazino[3,4-b] [1,3,4]thiadiazin-4-ones, and trans-3,4-dihydro-2H-[1,3,4]thiadiazino[2,3-b]quinazolin-10-one. trans-6,7-Dihydro-5H-[1,2,4]triazolo[3,4-b][1,3,4]thiadiazines isomerize slowly in CDCl(3) and more rapidly in DMSO-d(6) into the corresponding cis-stereoisomers. The other trans-6,7-dihydro-1 1,3,4]thiadiazines isomerize also in DMSO-d6 into the corresponding cis-stereoisomers. Pyrolytic conversion of these heterocyclic condensed dihydrothiadiazines into their corresponding pyrazolo[5,1-b][1,2,4]triazoles, pyrazolo[5,1-c][1,2,4]triazin-4-ones and pyrazolo[4,3-b]quinazolin-9-ones via desulfurization ring contraction is described. (C) 2011 Elsevier Ltd. All rights reserved.
引用
收藏
页码：6259 / 6274
页数：16
相关论文
共 50 条
  • [31] Synthesis of Constrained Head-to-Tail Cyclic Tetrapeptides by an Imine-Induced Ring-Closing/Contraction Strategy
    Wong, Clarence T. T.
    Lam, Hiu Yung
    Song, Tao
    Chen, Guanhua
    Li, Xuechen
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2013, 52 (39) : 10212 - 10215
  • [32] Stereoselective Synthesis of Contiguous Cyclopropylaziridines: Enabling the Construction of Versatile Chiral Molecules Including γ-Lactams via Ring-Opening Reactions
    Han, Jiho
    Ha, Hyun-Joon
    Yang, Jung Woon
    ADVANCED SYNTHESIS & CATALYSIS, 2023, 365 (12) : 1970 - 1976
  • [33] Synthesis of γ,δ-Aziridino α-Amino Acid Derivatives and their Stereoselective Ring Transformation to 2-(Aminomethyl)-1-aminocyclopropanecarboxylic Acid Derivatives
    De Brabandere, Stijn
    Mangelinckx, Sven
    Kadam, Santosh T.
    Nural, Yahya
    Augustyns, Koen
    Van der Veken, Pieter
    Tornroos, Karl W.
    De Kimpe, Norbert
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2014, 2014 (06) : 1220 - 1226
  • [34] One-Pot Stereoselective Double Intramolecular Oxymercuration: Synthesis of Four Isomers of an Unsymmetrical Bis-Tetrahydrofuran Ring System
    Mohapatra, Debendra K.
    Naidu, P. Ramesh
    Reddy, D. Srinivas
    Nayak, Sabita
    Mohapatra, Seetaram
    EUROPEAN JOURNAL OF ORGANIC CHEMISTRY, 2010, 2010 (32) : 6263 - 6268
  • [35] STEREOSELECTIVE SYNTHESIS OF THE A-RING OF ARMATOL A FROM A BROMO-SUBSTITUTED CHIRAL BUILDING BLOCK BASED ON IRELAND-CLAISEN REARRANGEMENT AND RING-CLOSING OLEFIN METATHESIS
    Hirose, Yuta
    Fujiwara, Kenshu
    Saito, Takafumi
    Katoono, Ryo
    Suzuki, Takanori
    HETEROCYCLES, 2015, 91 (01) : 76 - 103
  • [36] Stereoselective Synthesis of 1,n-Dicarbonyl Compounds Through Palladium-Catalyzed Ring Opening/Isomerization of Densely Substituted Cyclopropanols
    Teschers, Charlotte S.
    Cohen, Anthony
    Marek, Ilan
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2025, 64 (06)
  • [37] Rhodium(II) acetate-catalyzed stereoselective synthesis, SAR and anti-HIV activity of novel oxindoles bearing cyclopropane ring
    Kumari, Garima
    Nutan
    Modi, Manoj
    Gupta, Satish K.
    Singh, Ramendra K.
    EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY, 2011, 46 (04) : 1181 - 1188
  • [38] Synthesis of α-Formylated N-Heterocycles and Their 1,1-Diacetates from Inactivated Cyclic Amines Involving an Oxidative Ring Contraction
    Wang, Fang
    He, Yan
    Tian, Miaomiao
    Zhang, Xinying
    Fan, Xuesen
    ORGANIC LETTERS, 2018, 20 (03) : 864 - 867
  • [39] N-Bromosuccinimide-Induced Aminocyclization-Aziridine Ring-Expansion Cascade: An Asymmetric and Highly Stereoselective Approach toward the Synthesis of Azepane
    Zhou, Jing
    Yeung, Ying-Yeung
    ORGANIC LETTERS, 2014, 16 (08) : 2134 - 2137
  • [40] Switchable Bronsted Acid-Catalyzed Ring Contraction of Cyclooctatetraene Oxide Towards the Enantioselective Synthesis of Cycloheptatrienyl-Substituted Homoallylic Alcohols and Oxaborinanes
    Sendra, Jana
    Salvado, Oriol
    Pedron, Manuel
    Reyes, Efraim
    Tejero, Tomas
    Fernandez, Elena
    Merino, Pedro
    Vicario, Jose L.
    ADVANCED SYNTHESIS & CATALYSIS, 2023, 365 (07) : 1058 - 1071
12345