메뉴 건너뛰기




Volumn 14, Issue 3, 2010, Pages 463-471

Multicomponent reactions of amines with aldehydes and H2S as efficient route to heterocycles and thioaza macrocycles

Author keywords

Aldehydes; Amines; Hydrogen sulfide; Macroheterocycles; MCR; Multicomponent reactions; X ray analysis

Indexed keywords

ALDEHYDE; AMINE; AZETIDINE DERIVATIVE; CYCLOOCTANE DERIVATIVE; HYDROGEN SULFIDE; THIADIAZINE DERIVATIVE;

EID: 78650177341     PISSN: 13811991     EISSN: None     Source Type: Journal    
DOI: 10.1007/s11030-010-9248-3     Document Type: Article
Times cited : (32)

References (37)
  • 1
    • 33744916975 scopus 로고    scopus 로고
    • Multicomponent cascade heterocyclisation as a promising route to targeted synthesis of polyfunctional pyridines
    • DOI 10.1070/RC2003v072n01ABEH000764
    • VP Litvinov 2003 Multicomponent cascade heterocyclization as a promising route to targeted synthesis of polyfunctional pyridines Russ Chem Rev 72 69 85 10.1070/RC2003v072n01ABEH000764 1:CAS:528:DC%2BD3sXkt1Kkurc%3D 10.1070/RC2003v072n01ABEH000764 (Pubitemid 44352214)
    • (2003) Russian Chemical Reviews , vol.72 , Issue.1 , pp. 69-85
    • Litvinov, V.P.1
  • 3
    • 37049118476 scopus 로고
    • The conformational analysis of saturated heterocycles Part XLV N-Alkyldihydro-1,3,5-dithiazines and N-alkyltetrahydro-1,3,5-thiadiazines
    • 10.1039/P29720000674
    • L Angiolini RP Duke AY Jones AR Katritzky 1972 The conformational analysis of saturated heterocycles Part XLV N-Alkyldihydro-1,3,5-dithiazines and N-alkyltetrahydro-1,3,5-thiadiazines J Chem Soc Perkin Trans II 674 680 10.1039/P29720000674
    • (1972) J Chem Soc Perkin Trans , vol.2 , pp. 674-680
    • Angiolini, L.1    Duke, R.P.2    Jones, A.Y.3    Katritzky, A.R.4
  • 5
    • 0036354668 scopus 로고    scopus 로고
    • Structure of products of reaction between benzoylacetylene and 1,5-diphenyldithiobiuret
    • 10.1023/A:1014859410679 1:CAS:528:DC%2BD38XksFCjt7g%3D 10.1023/A:1014859410679
    • TE Glotova AS Nakhmanovich AI Albanov NI Protsuk TV Nizovtseva VA Lopyrev 2002 Structure of products of reaction between benzoylacetylene and 1,5-diphenyldithiobiuret Chem Heterocycl Compd 38 74 78 10.1023/A:1014859410679 1:CAS:528:DC%2BD38XksFCjt7g%3D 10.1023/A:1014859410679
    • (2002) Chem Heterocycl Compd , vol.38 , pp. 74-78
    • Glotova, T.E.1    Nakhmanovich, A.S.2    Albanov, A.I.3    Protsuk, N.I.4    Nizovtseva, T.V.5    Lopyrev, V.A.6
  • 6
    • 7244232894 scopus 로고    scopus 로고
    • Synthesis and reactions of 2-benzoylmethyl-2-phenyl-4,6-di(phenylimino)- 5h- 1,3,5-dithiazinium perchlorate
    • DOI 10.1023/B:RUJO.0000045913.55155.81
    • TE Glotova NI Protsuk MU Dvorko AI Albanov 2004 Synthesis and reactions of 2-benzoylmethyl-2-phenyl-4,6-di(phenylimino)-5H-1,3,5-dithiazinium perchlorate Russ J Org Chem 40 1222 1223 10.1023/B:RUJO.0000045913.55155.81 1:CAS:528:DC%2BD2cXovFalurY%3D 10.1023/B:RUJO.0000045913.55155.81 (Pubitemid 39434536)
    • (2004) Russian Journal of Organic Chemistry , vol.40 , Issue.8 , pp. 1222-1223
    • Glotova, T.E.1    Protsuk, N.I.2    Dvorko, M.Y.3    Albanov, A.I.4
  • 7
    • 3543025118 scopus 로고    scopus 로고
    • Synthesis of new 1,3,5-dithiazine derivatives
    • 10.1023/B:RUJO.0000013151.76841 1:CAS:528:DC%2BD2cXmtlGkug%3D%3D 10.1023/B:RUJO.0000013151.76841.c3
    • TE Glotova NI Protsuk AI Albanov 2003 Synthesis of new 1,3,5-dithiazine derivatives Russ J Org Chem 39 1681 1682 10.1023/B:RUJO.0000013151.76841 1:CAS:528:DC%2BD2cXmtlGkug%3D%3D 10.1023/B:RUJO.0000013151.76841.c3
    • (2003) Russ J Org Chem , vol.39 , pp. 1681-1682
    • Glotova, T.E.1    Protsuk, N.I.2    Albanov, A.I.3
  • 8
    • 84986526611 scopus 로고
    • 1. 4H-1,3,5-dithiazines, a new class of heterocycles
    • 10.1055/s-1977-24319
    • 1. 4H-1,3,5-dithiazines, a new class of heterocycles Synthesis 3 193 194 10.1055/s-1977-24319
    • (1977) Synthesis , vol.3 , pp. 193-194
    • Giordano, C.1    Belli, A.2
  • 9
    • 85056053198 scopus 로고
    • Synthesis and reactions of α-haloalkyl isocyanates
    • 10.1055/s-1980-28930 10.1055/s-1980-28930
    • VI Gorbatenko LI Samarai 1980 Synthesis and reactions of α-haloalkyl isocyanates Synthesis 2 85 100 10.1055/s-1980-28930 10.1055/s-1980-28930
    • (1980) Synthesis , vol.2 , pp. 85-100
    • Gorbatenko, V.I.1    Samarai, L.I.2
  • 10
    • 77249103002 scopus 로고
    • Synthesis, thermal stability and mass spectra of 2-trihalomethyl-1,3,5- dithiazin-4-ones and their 2,3-dihydroderivatives
    • 10.1007/BF01170751
    • MV Vovk IG Krainikova VI Dorokhov 1995 Synthesis, thermal stability and mass spectra of 2-trihalomethyl-1,3,5-dithiazin-4-ones and their 2,3-dihydroderivatives Chem Heterocycl Compd 7 868 872 10.1007/BF01170751
    • (1995) Chem Heterocycl Compd , vol.7 , pp. 868-872
    • Vovk, M.V.1    Krainikova, I.G.2    Dorokhov, V.I.3
  • 11
    • 0010217526 scopus 로고
    • 1-Cyanalkyliden-substituierte 1,3-dithietanone als cyanthioketen- äquivalente. Umsetzung zu 1,3,5-Dithiazin-4-onen und 2-Azetidinthionen
    • 10.1002/cber.19841170614 1:CAS:528:DyaL2cXkvFSrsr4%3D 10.1002/cber.19841170614
    • E Schaumann U Wriede G Adiwidjaja 1984 1-Cyanalkyliden-substituierte 1,3-dithietanone als cyanthioketen-äquivalente. Umsetzung zu 1,3,5-Dithiazin-4-onen und 2-Azetidinthionen Chem Ber 117 2205 2225 10.1002/cber.19841170614 1:CAS:528:DyaL2cXkvFSrsr4%3D 10.1002/cber.19841170614
    • (1984) Chem Ber , vol.117 , pp. 2205-2225
    • Schaumann, E.1    Wriede, U.2    Adiwidjaja, G.3
  • 15
    • 0010398812 scopus 로고
    • Eight-membered ring heterocycles from primary amines, hydrogen sulfide, and formaldehyde
    • 10.1021/jo01053a024 10.1021/jo01053a024
    • JL Nelson C Kenneth EY Andrew 1962 Eight-membered ring heterocycles from primary amines, hydrogen sulfide, and formaldehyde J Org Chem 27 2019 2021 10.1021/jo01053a024 10.1021/jo01053a024
    • (1962) J Org Chem , vol.27 , pp. 2019-2021
    • Nelson, J.L.1    Kenneth, C.2    Andrew, E.Y.3
  • 16
    • 37049135545 scopus 로고
    • NMR studies of rate processes and conformations. Conformational rate processes in eight-membered heterocycles
    • doi: 10.1039/C19660000803
    • Lehn JM, Riddell FG (1966) NMR studies of rate processes and conformations. Conformational rate processes in eight-membered heterocycles. Chem Comm:803-805. doi: 10.1039/C19660000803
    • (1966) Chem Comm , pp. 803-805
    • Lehn, J.M.1    Riddell, F.G.2
  • 17
    • 37049143423 scopus 로고
    • The action of hydrogen sulphide on certain methyleneimines
    • doi: 10.1039/JR9500000208
    • Braithwaite ER, Graymore J (1950) The action of hydrogen sulphide on certain methyleneimines. Part I. J Chem Soc:208-210. doi: 10.1039/JR9500000208
    • (1950) Part I. J Chem Soc , pp. 208-210
    • Braithwaite, E.R.1    Graymore, J.2
  • 18
    • 37049152071 scopus 로고
    • The action of hydrogen sulphide on certain methyleneimines. Part II
    • doi: 10.1039/JR9530000143
    • Braithwaite ER, Graymore J (1953) The action of hydrogen sulphide on certain methyleneimines. Part II. J Chem Soc:143-145. doi: 10.1039/JR9530000143
    • (1953) J Chem Soc , pp. 143-145
    • Braithwaite, E.R.1    Graymore, J.2
  • 19
    • 37049161734 scopus 로고
    • The action of hydrogen sulphide on certain aromatic amines in the presence of formaldehyde
    • doi: 10.1039/JR9530004089
    • Collins D, Graymore J (1953) The action of hydrogen sulphide on certain aromatic amines in the presence of formaldehyde. J Chem Soc:4089-4090. doi: 10.1039/JR9530004089
    • (1953) J Chem Soc , pp. 4089-4090
    • Collins, D.1    Graymore, J.2
  • 21
    • 34547144706 scopus 로고    scopus 로고
    • Thiomethylation of amino alcohols using formaldehyde and hydrogen sulfide
    • 10.1134/S1070428007060218 1:CAS:528:DC%2BD2sXnslSgtLc%3D 10.1134/S1070428007060218
    • VR Akhmetova GR Nadyrgulova TV Tyumkina ZA Starikova MYu Antipin RV Kunakova UM Dzhemilev 2007 Thiomethylation of amino alcohols using formaldehyde and hydrogen sulfide Russ J Org Chem 43 918 925 10.1134/S1070428007060218 1:CAS:528:DC%2BD2sXnslSgtLc%3D 10.1134/S1070428007060218
    • (2007) Russ J Org Chem , vol.43 , pp. 918-925
    • Akhmetova, V.R.1    Nadyrgulova, G.R.2    Tyumkina, T.V.3    Starikova, Z.A.4    Myu, A.5    Kunakova, R.V.6    Dzhemilev, U.M.7
  • 23
    • 0348120839 scopus 로고
    • Derivate des thioformaldehydes
    • 10.1002/cber.188601902155
    • A Wohl 1886 Derivate des thioformaldehydes Ber Deutsch Chem Ges 19 2344 10.1002/cber.188601902155
    • (1886) Ber Deutsch Chem Ges , vol.19 , pp. 2344
    • Wohl, A.1
  • 24
    • 0042236983 scopus 로고    scopus 로고
    • Aminoacid-based dithiazines: Synthesis and photofragmentation of their benzaldehyde adducts
    • 10.1021/ol0268790 1:CAS:528:DC%2BD38XotVegtbw%3D 10.1021/ol0268790 12423103
    • AN Kurchan AG Kutateladze 2002 Aminoacid-based dithiazines: synthesis and photofragmentation of their benzaldehyde adducts Org Lett 4 4129 4131 10.1021/ol0268790 1:CAS:528:DC%2BD38XotVegtbw%3D 10.1021/ol0268790 12423103
    • (2002) Org Lett , vol.4 , pp. 4129-4131
    • Kurchan, A.N.1    Kutateladze, A.G.2
  • 26
    • 0345742320 scopus 로고    scopus 로고
    • Thiomethylation of aromatic amines: Efficient method for the synthesis of heterocyclic compounds
    • DOI 10.1023/A:1026021124424
    • SR Khafizova VR Akhmetova RV Kunakova UM Dzhemilev 2003 Thiomethylation of aromatic amines: efficient method for the synthesis of heterocyclic compounds Russ Chem Bull 52 1817 1821 10.1023/A:1026021124424 1:CAS:528: DC%2BD3sXnvFagtL0%3D 10.1023/A:1026021124424 (Pubitemid 38096038)
    • (2003) Russian Chemical Bulletin , vol.52 , Issue.8 , pp. 1817-1821
    • Khafizova, S.R.1    Akhmetova, V.R.2    Kunakova, R.V.3    Dzhemilev, U.M.4
  • 27
    • 37049174447 scopus 로고
    • The interaction of ammonium and alkylammonium sulphides with aqueous formaldehyde
    • doi: 10.1039/JR9320001142
    • Le Fevre CS, Le Fevre RIW (1932) The interaction of ammonium and alkylammonium sulphides with aqueous formaldehyde. J Chem Soc:1142-1148. doi: 10.1039/JR9320001142
    • (1932) J Chem Soc , pp. 1142-1148
    • Le Fevre, C.S.1    Fevre Riw, L.2
  • 28
    • 37049050225 scopus 로고
    • The condensation of azomethines with hydrogen sulphide and aldehydes
    • doi: 10.1039/JR9570000009
    • Collins D, Graymore J (1957) The condensation of azomethines with hydrogen sulphide and aldehydes. J Chem Soc:9-10. doi: 10.1039/JR9570000009
    • (1957) J Chem Soc , pp. 9-10
    • Collins, D.1    Graymore, J.2
  • 29
    • 1842442383 scopus 로고
    • The basicity of dihydrothia-azetidines, and tetrahydrothiadiazines
    • doi: 10.1039/JR9580002888
    • Collins D, Graymore J (1958) The basicity of dihydrothia-azetidines, and tetrahydrothiadiazines. J Chem Soc:2893. doi: 10.1039/JR9580002888
    • (1958) J Chem Soc , pp. 2893
    • Collins, D.1    Graymore, J.2
  • 31
    • 0001715193 scopus 로고
    • Über die Synthese von 1,3,4-Thiadiazolidinen und 1,3,4-Thiadiazolen
    • 10.1002/prac.19590080505 1:CAS:528:DyaF3cXhtFSnu7k%3D 10.1002/prac.19590080505
    • K Ruhlmann 1959 Über die Synthese von 1,3,4-Thiadiazolidinen und 1,3,4-Thiadiazolen J Prakt Chem 8 285 291 10.1002/prac.19590080505 1:CAS:528:DyaF3cXhtFSnu7k%3D 10.1002/prac.19590080505
    • (1959) J Prakt Chem , vol.8 , pp. 285-291
    • Ruhlmann, K.1
  • 32
    • 14944366488 scopus 로고    scopus 로고
    • Multicomponent heterocyclization of hydrazine, hydrogen sulfide, and formaldehyde
    • DOI 10.1007/s11172-005-0023-z
    • SR Khafizova VR Akhmetova TV Tyumkina LM Khalilov RV Kunakova UM Dzhemilev 2004 Multicomponent heterocyclization of hydrazine, hydrogen sulfide, and formaldehyde Russ Chem Bull 53 1717 1721 10.1007/s11172-005-0023-z 1:CAS:528:DC%2BD2MXmtlam 10.1007/s11172-005-0023-z (Pubitemid 40363233)
    • (2004) Russian Chemical Bulletin , vol.53 , Issue.8 , pp. 1717-1721
    • Khafizova, S.R.1    Akhmetova, V.R.2    Tyumkina, T.V.3    Khalilov, L.M.4    Kunakova, R.V.5    Dzhemilev, U.M.6
  • 34
    • 53349156971 scopus 로고    scopus 로고
    • Stereoelectronic effects in N-C-S and N-N-C systems: Experimental and ab initio AIM study
    • 10.1021/jp800384k 1:CAS:528:DC%2BD1cXlslSmtrw%3D
    • IS Bushmarinov MY Antipin VR Akhmetova GR Nadyrgulova KA Lyssenko 2008 Stereoelectronic effects in N-C-S and N-N-C systems: experimental and ab initio AIM study J Phys Chem 112 5017 5023 10.1021/jp800384k 1:CAS:528: DC%2BD1cXlslSmtrw%3D
    • (2008) J Phys Chem , vol.112 , pp. 5017-5023
    • Bushmarinov, I.S.1    Antipin, M.Y.2    Akhmetova, V.R.3    Nadyrgulova, G.R.4    Lyssenko, K.A.5


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.