메뉴 건너뛰기




Volumn 33, Issue 8, 2003, Pages 1341-1357

New phosphono substituted 3- and 5-membered rings starting from 3(2-thienyl)acrylonitriles and α-phosphoryl carbanions

Author keywords

Acrylonitriles; Michael addition; Phosphono substituted heterocycles; Wittig Horner synthons

Indexed keywords

3 (2 THIENYL)ACRYLONITRILE; ACETIC ACID DERIVATIVE; ACRYLONITRILE; ALPHA PHOSPHORYL CARBANION; BASE; DIETHYL ALPHA CYANOMETHYL PHOSPHONATE; DIETHYL PHOSPHONOACETATE; ETHYL 3 (2 THIENYL)ACRYLOCYANOACETATE; ETHYLENE; HETEROCYCLIC COMPOUND; PHOSPHONIC ACID DERIVATIVE; PHOSPHONIUM DERIVATIVE; PHOSPHORANE DERIVATIVE; PHOSPHORUS DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0037966866     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1081/SCC-120018694     Document Type: Article
Times cited : (13)

References (40)
  • 1
    • 2542554996 scopus 로고    scopus 로고
    • Comparative behaviour 2,6-di-tert-butyl- and 2,3-dichloro-5,6-dicyano-1,4-benzoquinones with some phosphorus reagents
    • (a) Abdou, W.M.; Salem, M.A.I.; Sediek, A.A. Comparative behaviour 2,6-di-tert-butyl- and 2,3-dichloro-5,6-dicyano-1,4-benzoquinones with some phosphorus reagents. J. Chem. Res. (S) 1998, 28-29; (M), 1998, 327-339;
    • (1998) J. Chem. Res. (S) , pp. 28-29
    • Abdou, W.M.1    Salem, M.A.I.2    Sediek, A.A.3
  • 2
    • 2542554996 scopus 로고    scopus 로고
    • (a) Abdou, W.M.; Salem, M.A.I.; Sediek, A.A. Comparative behaviour 2,6-di-tert-butyl- and 2,3-dichloro-5,6-dicyano-1,4-benzoquinones with some phosphorus reagents. J. Chem. Res. 1998, 28-29; (M), 1998, 327-339;
    • (1998) J. Chem. Res. (M) , pp. 327-339
  • 3
    • 0038296286 scopus 로고    scopus 로고
    • The reactions of alkyl phosphites with α-β-unsaturated carbon-nitrogen multiple-bonds: 2-Benzylidenecyanomethyl-1,3-benzothiazole and α-benzil monoxime
    • (b) Ganoub, N.A.; Abdou, W.M.; Shaddy, A.A.M. The reactions of alkyl phosphites with α-β-unsaturated carbon-nitrogen multiple-bonds: 2-Benzylidenecyanomethyl-1,3-benzothiazole and α-benzil monoxime. Phosphorus, Sulfur and Silicon 1998, 132, 109-122;
    • (1998) Phosphorus, Sulfur, Silicon , vol.132 , pp. 109-122
    • Ganoub, N.A.1    Abdou, W.M.2    Shaddy, A.A.M.3
  • 4
    • 0038210324 scopus 로고
    • Reactions of trialkyl phosphites with 5-p-chlorophenyl-4-cyano-1,2-dithiole-3-thione, and with 5-phenyl-1,2,4-dithiazol-3-one and its thione derivatives
    • (c) Abdou, W.M.; Hennawy, I.T.; El-Khoshnieh, Y.O. Reactions of trialkyl phosphites with 5-p-chlorophenyl-4-cyano-1,2-dithiole-3-thione, and with 5-phenyl-1,2,4-dithiazol-3-one and its thione derivatives. J. Chem. Research (S) 1995, 50-51; (M), 1995, 442-451;
    • (1995) J. Chem. Research (S) , pp. 50-51
    • Abdou, W.M.1    Hennawy, I.T.2    El-Khoshnieh, Y.O.3
  • 5
    • 0038549126 scopus 로고
    • (c) Abdou, W.M.; Hennawy, I.T.; El-Khoshnieh, Y.O. Reactions of trialkyl phosphites with 5-p-chlorophenyl-4-cyano-1,2-dithiole-3-thione, and with 5-phenyl-1,2,4-dithiazol-3-one and its thione derivatives. J. Chem. Research (S) 1995, 50-51; (M), 1995, 442-451;
    • (1995) J. Chem. Research (M) , pp. 442-451
  • 6
    • 0001739327 scopus 로고
    • Reactions of tetracynoethylene with ter- and pentavalent phosphorus reagents
    • (d) Abdou, W.M.; Ganoub, N.A.F. Reactions of tetracynoethylene with ter- and pentavalent phosphorus reagents. Heterocyclic Commun. 1995, 1, 387-393;
    • (1995) Heterocyclic Commun. , vol.1 , pp. 387-393
    • Abdou, W.M.1    Ganoub, N.A.F.2
  • 7
    • 43049105820 scopus 로고
    • The reaction of α-β-unsaturated nitriles with alkyl phosphites and phosphorus ylides
    • (e) Mahran, M.R.; Abdou, W.M.; Abd El-Rahman, N.M.; Khidre, M.D. The reaction of α-β-unsaturated nitriles with alkyl phosphites and phosphorus ylides. Heteroatom Chem. 1992, 3, 93-99;
    • (1992) Heteroatom Chem. , vol.3 , pp. 93-99
    • Mahran, M.R.1    Abdou, W.M.2    Abd El-Rahman, N.M.3    Khidre, M.D.4
  • 8
    • 84950029932 scopus 로고
    • The behaviour of 1-dicyanomethylene-acenaphthen-2-one and 1-dicyanomethylene-3-indanone toward attack by alkyl phosphites
    • (f) Mahran, M.R.; Abdou, W.M.; Ganoub, N.A.; Abdallah, H.A. The behaviour of 1-dicyanomethylene-acenaphthen-2-one and 1-dicyanomethylene-3-indanone toward attack by alkyl phosphites. Phosphorus, Sulfur and Silicon 1991, 57, 217-225;
    • (1991) Phosphorus, Sulfur, Silicon , vol.57 , pp. 217-225
    • Mahran, M.R.1    Abdou, W.M.2    Ganoub, N.A.3    Abdallah, H.A.4
  • 9
    • 0037872775 scopus 로고
    • The reaction of 10-dicynomethylene 9(10H)-phenanthrenone with alkyl phosphites
    • (g) Abdou, W.M.; Ganoub, N.A.F.; Mahran, M.R. The reaction of 10-dicynomethylene 9(10H)-phenanthrenone with alkyl phosphites. J. Chem. Soc. (Jpn) 1991, 64, 747-749;
    • (1991) J. Chem. Soc. (Jpn). , vol.64 , pp. 747-749
    • Abdou, W.M.1    Ganoub, N.A.F.2    Mahran, M.R.3
  • 10
    • 0007806917 scopus 로고
    • The reaction of furfurylidenemalonitrile with alkyl phosphites
    • (h) Abdou, W.M.; Khidre, M.D.; Mahran, M.R. The reaction of furfurylidenemalonitrile with alkyl phosphites. J. Prak. Chem. 1990, 332, 1029-1034.
    • (1990) J. Prak. Chem. , vol.332 , pp. 1029-1034
    • Abdou, W.M.1    Khidre, M.D.2    Mahran, M.R.3
  • 11
    • 0032581644 scopus 로고    scopus 로고
    • Selective addition of Wittig reagents to bifunctionalized compounds. Condensation of 3-phenyl (2-benzothiazolyl)acrylonitrile with phosphorus ylides
    • (a) Abdou, W.M.; Ganoub, N.A.F.; Shaddy, A.M. Selective addition of Wittig reagents to bifunctionalized compounds. Condensation of 3-phenyl (2-benzothiazolyl)acrylonitrile with phosphorus ylides. Tetrahedron 1998, 54, 9079-9088;
    • (1998) Tetrahedron , vol.54 , pp. 9079-9088
    • Abdou, W.M.1    Ganoub, N.A.F.2    Shaddy, A.M.3
  • 12
    • 0030886050 scopus 로고    scopus 로고
    • Reactions of alkylidenephosphoranes with symmetrically p-quinones
    • (b) Abdou, W.M.; Salem, M.A.I.; Sediek, A.A. Reactions of alkylidenephosphoranes with symmetrically p-quinones. Tetrahedron 1997, 53, 13945-13958;
    • (1997) Tetrahedron , vol.53 , pp. 13945-13958
    • Abdou, W.M.1    Salem, M.A.I.2    Sediek, A.A.3
  • 13
    • 84906480942 scopus 로고
    • Comparative chemical studies of the behaviour of 4-cyano-1,2-dithioles in analogy with 1,2,4-dithiazoles toward stable phosphonium ylides
    • (c) Abdou, W.M.; Ganoub. N.A.F. Comparative chemical studies of the behaviour of 4-cyano-1,2-dithioles in analogy with 1,2,4-dithiazoles toward stable phosphonium ylides. Phosphorus, Sulfur and Silicon 1995, 105, 63-71;
    • (1995) Phosphorus, Sulfur and Silicon , vol.105 , pp. 63-71
    • Abdou, W.M.1    Ganoub, N.A.F.2
  • 14
    • 84986366215 scopus 로고
    • Wittig reaction of 1-dicyanomethyleneacenaphthen-2-one
    • (d) Abdou, W.M.; Ganoub, N.A.F. Wittig reaction of 1-dicyanomethyleneacenaphthen-2-one. Heteroatom Chemistry 1992, 3, 133-137;
    • (1992) Heteroatom Chemistry , vol.3 , pp. 133-137
    • Abdou, W.M.1    Ganoub, N.A.F.2
  • 15
    • 0026121866 scopus 로고
    • Reaction of α-β-unsaturated nitriles with phosphorus ylides
    • (e) Abdou, W.M.; Ganoub, N.A.F. Reaction of α-β-unsaturated nitriles with phosphorus ylides. Chemistry and Industry (London) 1991, 217-218.
    • (1991) Chemistry Industry (London) , pp. 217-218
    • Abdou, W.M.1    Ganoub, N.A.F.2
  • 18
    • 0001848341 scopus 로고
    • The Wittig olefination reaction and modifications involving phosphoryl-stabilized carbanions. Stereochemistry, mechanism, and selected synthetic aspects
    • and references therein
    • (a) Maryanoff, B.E.; Reitz, A.B. The Wittig olefination reaction and modifications involving phosphoryl-stabilized carbanions. Stereochemistry, mechanism, and selected synthetic aspects. Chem. Rev. 1989, 89, 863-927 and references therein;
    • (1989) Chem. Rev. , vol.89 , pp. 863-927
    • Maryanoff, B.E.1    Reitz, A.B.2
  • 19
    • 0002166172 scopus 로고
    • Transformations via phosphorus-stabilized anions. 2: PO-activated olefination
    • Cadogan, J.I.G., Ed.; Academic Press: London, Chapter 3
    • (b) Walker, B.J. Transformations via phosphorus-stabilized anions. 2: PO-activated olefination. In Organic Phosphorus Reagents in Organic Synthesis; Cadogan, J.I.G., Ed.; Academic Press: London, 1979; Chapter 3, pp. 155-206.
    • (1979) Organic Phosphorus Reagents in Organic Synthesis , pp. 155-206
    • Walker, B.J.1
  • 20
    • 0037872774 scopus 로고
    • Reactions of 3-alkyl and alicyclic α-enones with phosphorylated anions
    • (a) Bernard, D.; Jacquelina, S. Reactions of 3-alkyl and alicyclic α-enones with phosphorylated anions. Tetrahetron 1977, 33, 413-417;
    • (1977) Tetrahetron , vol.33 , pp. 413-417
    • Bernard, D.1    Jacquelina, S.2
  • 21
    • 0000833445 scopus 로고
    • Reactions of 3-aryl α-enones with phosphorylated anions
    • (b) Moncef, C.; Bernard, D.; Trong Anh, N.; Jacqueline, S. Reactions of 3-aryl α-enones with phosphorylated anions. Tetrahedron 1977, 33, 409-412.
    • (1977) Tetrahedron , vol.33 , pp. 409-412
    • Moncef, C.1    Bernard, D.2    Trong Anh, N.3    Jacqueline, S.4
  • 22
    • 21344488418 scopus 로고
    • The behavior of 5-(4-pyridyl)-2-thiono-1,3,4-oxadioazole towards Wittig-Horner reagents
    • (a) Boulos, L.S.; Yakout, E.M.A. The behavior of 5-(4-pyridyl)-2-thiono-1,3,4-oxadioazole towards Wittig-Horner reagents. Phosphorus, Sulfur and Silicon 1993, 84, 35-38;
    • (1993) Phosphorus, Sulfur, Silicon , vol.84 , pp. 35-38
    • Boulos, L.S.1    Yakout, E.M.A.2
  • 24
    • 0010640086 scopus 로고
    • Convenient synthesis of both the anomers of ethyl (2,3,4,6-tetra-o-benzyl-D-glucopyranosyl) acetate
    • (a) Monti, D.; Gramatica, P.; Speranza, G.; Manitto, P.A Convenient synthesis of both the anomers of ethyl (2,3,4,6-tetra-o-benzyl-D-glucopyranosyl) acetate. Tetrahedron Lett. 1987, 28, 5047-5048;
    • (1987) Tetrahedron Lett. , vol.28 , pp. 5047-5048
    • Monti, D.1    Gramatica, P.2    Speranza, G.3    Manitto, P.A.4
  • 25
    • 0033415907 scopus 로고    scopus 로고
    • The reaction of Wittig-Horner reagents and alkyl phosphites with 1,2-naphthoquinone-1-benzimide
    • (b) Arsanious, M.H.N. The reaction of Wittig-Horner reagents and alkyl phosphites with 1,2-naphthoquinone-1-benzimide. Monatsh. Für Chemie 1999, 130, 921-928.
    • (1999) Monatsh. Für Chemie , vol.130 , pp. 921-928
    • Arsanious, M.H.N.1
  • 26
    • 0000755077 scopus 로고
    • Derivatives of dialkoxy phosphoacetonitriles
    • Bodnarchuk, N.D.; Malovik, V.V.; Derkarch, G.I. Derivatives of dialkoxy phosphoacetonitriles. Zh. Obsh. Khim. 1969, 39, 168-172; C. A. 1969, 70, 96857.
    • (1969) Zh. Obsh. Khim. , vol.39 , pp. 168-172
    • Bodnarchuk, N.D.1    Malovik, V.V.2    Derkarch, G.I.3
  • 27
    • 85012703633 scopus 로고
    • Bodnarchuk, N.D.; Malovik, V.V.; Derkarch, G.I. Derivatives of dialkoxy phosphoacetonitriles. Zh. Obsh. Khim. 1969, 39, 168-172; C.A. 1969, 70, 96857.
    • (1969) C. A. , vol.70 , pp. 96857
  • 30
    • 0000348137 scopus 로고
    • Reaction of alkylidene triphenylphosphoranes with quinones
    • Bestmann, H.J.; Lang, H.J. Reaction of alkylidene triphenylphosphoranes with quinones. Tetrahedron 1969, 25, 2101-2106.
    • (1969) Tetrahedron , vol.25 , pp. 2101-2106
    • Bestmann, H.J.1    Lang, H.J.2
  • 31
    • 37049057740 scopus 로고
    • The addition of Wittig reagents to activated carbon-carbon double bonds
    • Trippet, S. The addition of Wittig reagents to activated carbon-carbon double bonds. J. Chem. Soc. 1962, 4733-4734.
    • (1962) J. Chem. Soc. , pp. 4733-4734
    • Trippet, S.1
  • 32
    • 37049115433 scopus 로고
    • Formyl olefination of carbonyl compounds
    • (a) Nagata, W.; Hayase, Y. Formyl olefination of carbonyl compounds. J. Chem. Soc. (C) 1969, 460-466;
    • (1969) J. Chem. Soc. (C) , pp. 460-466
    • Nagata, W.1    Hayase, Y.2
  • 33
    • 85202323704 scopus 로고
    • Esrers of β-ethoxyvinylphosphonic, β-propoxyvinylphosphonic, β-butoxyvinylphosphonic, and β-hexoyvinyl-phosphonic acids
    • (b) Anisimov, K.M.; Kolobora, N.E.; Nesmeyanov, A.N. Esrers of β-ethoxyvinylphosphonic, β-propoxyvinylphosphonic, β-butoxyvinylphosphonic, and β-hexoyvinyl-phosphonic acids. Bull. Acad. Sci. USSR 1955, 213-220; C. A. 1956, 50, 3217;
    • (1955) Bull. Acad. Sci. USSR , pp. 213-220
    • Anisimov, K.M.1    Kolobora, N.E.2    Nesmeyanov, A.N.3
  • 34
    • 3643058056 scopus 로고
    • (b) Anisimov, K.M.; Kolobora, N.E.; Nesmeyanov, A.N. Esrers of β-ethoxyvinylphosphonic, β-propoxyvinylphosphonic, β-butoxyvinylphosphonic, and β-hexoyvinyl-phosphonic acids. Bull. Acad. Sci. USSR 1955, 213-220; C. A. 1956, 50, 3217;
    • (1956) C. A. , vol.50 , pp. 3217
  • 35
    • 17444403825 scopus 로고
    • The Wittig olefination reaction with carbonyl compounds other than aldehydes and ketones
    • (c) Murphy, P.J. The Wittig olefination reaction with carbonyl compounds other than aldehydes and ketones. Chem. Soc. Rev. 1988, 17, 1-30.
    • (1988) Chem. Soc. Rev. , vol.17 , pp. 1-30
    • Murphy, P.J.1
  • 36
    • 0038549088 scopus 로고
    • A new color reaction for the detection and estimation of dialkyl phosphites
    • Saunders, B.C.; Stark, B.P. A new color reaction for the detection and estimation of dialkyl phosphites. Tetrahedron 1958, 4, 197-198.
    • (1958) Tetrahedron , vol.4 , pp. 197-198
    • Saunders, B.C.1    Stark, B.P.2
  • 37
    • 0037534947 scopus 로고
    • Properties of molecules
    • The English Language Book Society and Longman Group Limited (England), 6th Ed.
    • (a) Finar, I.L. Properties of molecules. In Organic Chemistry, The Fundamental Principles; Vol. 1, pp. 28-67. The English Language Book Society and Longman Group Limited (England), 6th Ed.; 1975;
    • (1975) Organic Chemistry, The Fundamental Principles , vol.1 , pp. 28-67
    • Finar, I.L.1
  • 38
    • 84963165248 scopus 로고
    • Synthesis of new complex ylidenetriphenylphosphoranes from the reaction of arylidenemalonitriles with Wittig reagents
    • (b) Hafez, T.S.; Fahmy, A.A.; Atta, S.M. Sh. Synthesis of new complex ylidenetriphenylphosphoranes from the reaction of arylidenemalonitriles with Wittig reagents. Phosphorus, Sulfur and Silicon 1993, 84, 165-171.
    • (1993) Phosphorus, Sulfur and Silicon , vol.84 , pp. 165-171
    • Hafez, T.S.1    Fahmy, A.A.2    Atta, S.M.Sh.3
  • 39
    • 33947476360 scopus 로고
    • Synthesis of 3-hydroxypyridines. II. Preparation of unsaturated cyano esters and their reaction with diazomethane
    • Popp, F.D.; Catala, A. Synthesis of 3-hydroxypyridines. II. Preparation of unsaturated cyano esters and their reaction with diazomethane. J. Org. Chem. 1961, 26, 2738-2740.
    • (1961) J. Org. Chem. , vol.26 , pp. 2738-2740
    • Popp, F.D.1    Catala, A.2
  • 40
    • 0012780959 scopus 로고
    • Ylidenemalonitriles in thiophene ring annelations
    • Schneller, S.W.; Moore, D.R. Ylidenemalonitriles in thiophene ring annelations. J. Org. Chem. 1975, 40, 1840-1842.
    • (1975) J. Org. Chem. , vol.40 , pp. 1840-1842
    • Schneller, S.W.1    Moore, D.R.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.