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Journal of Heterocyclic Chemistry
Volumn 23, Issue 6, 1986, Pages 1757-1763
Convenient synthesis of substituted 3‐aminothiophene‐2‐carbonitriles from α‐acetylenic nitriles and their conversion to thieno[3,2‐d]pyrimidines
Author keywords

[No Author keywords available]
Indexed keywords

2,4 DIAMINO 6 PHENYLTHIENO[2,3 D]PYRIMIDINE; 3 AMINO 2 THIOPHENECARBONITRILE DERIVATIVE; NEW DRUG; THIENO[3,2 D]PYRIMIDINE DERIVATIVE; UNCLASSIFIED DRUG;
EID: 0022917593     PISSN: 0022152X     EISSN: 19435193     Source Type: Journal    
DOI: 10.1002/jhet.5570230631     Document Type: Article
Times cited : (34)
References (49)
  • 13
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    • German Patent 1,005,007
  • 15
    • 84986434220 scopus 로고    scopus 로고
    • British Patent 837,086, Farbwerke Hoechst Akt.‐Ges. vorm Meister Lucius and Bruning
  • 17
    • 84986434233 scopus 로고
    • The synthesis of various thieno[3,2‐d]pyrimidines from their most common precursors, the 3‐amino‐2‐carbalkoxythiophenes is described in the following:, Bull. Soc. Chim. France
    • (1970) , pp. 3630
    • Robba, M.1    Lecomte, J.‐M.2    Cugnon de Sevricourt, M.3
  • 21
    • 84986494523 scopus 로고
    • [e]
    • (1968) Ann. Chem. , vol.713 , pp. 143
  • 27
    • 84945078929 scopus 로고
    • Polyacetylenverbindungen, LX. Über die Kondensation von Acetylencarbonsäureestern mit Mercaptanen
    • [d] Cyclization of adducts obtained from α‐mercaptoacetates and α‐mercaptoketones with acetylenecarboxylic esters to give 3‐OH substituted thiophenes has been reported
    • (1964) Chemische Berichte , vol.97 , pp. 2109
    • Bohlman, F.1    Bresinsky, E.2
  • 29
    • 84986505652 scopus 로고
    • Acetylenic nitriles 3–5 [13a–13c] were obtained by ammonolysis of the commercially available corresponding acetylenic ethyl esters to the corresponding amides and dehydration to the nitriles with phosphorus oxychloride by slight modifications to the procedure reported in reference [13c]:, Bull. Soc. Chim. France
    • (1972) , pp. 2381
    • Texier, F.1    Carrie, R.2
  • 33
    • 84986516115 scopus 로고    scopus 로고
    • Conditions required for the amidine exchange implicated in such reactions are generally strenuous and the use of amidines other than formamidine have been studied relatively little [15a‐c]. Benzamidine has been condensed with 2,4‐diamino‐5‐cyano‐6‐dimethylaminopyridine to give a 7‐phenylpyrimido[4,5‐d]pyrimidine [15a] and acetamidine similarly reacts with 3‐amino‐4‐cyano‐5‐methylpyrazole to give 4‐amino‐3,6‐dimethylpyrazolo[3,4‐d]pyrimidine [15b]: J. Weinstock and V. D. Wichelhaus, French Patent 1,335,354 (August 6, 1963)
  • 36
    • 84986526006 scopus 로고
    • [c], J. Chem. Soc., Perkin Trans I
    • (1975) , pp. 345
    • Albert, A.1
  • 38
    • 33947468820 scopus 로고
    • THE SYNTHESIS OF ALKYLTHIOKETODIHYDROQUINAZOLINES FROM ANTHRANILICNITRILE.
    • This method is akin to an early report of the formation of 2‐alkyl‐4‐thionoquinazoline by the treatment of anthranilonitrile with an acid anhydride and sodium sulfide. That method involved in situ acylation of the amino group, conversion of the nitrile to the thioamide and condensation to the thioquinazoline as a one‐pot conversion
    • (1903) Journal of the American Chemical Society , vol.25 , pp. 372
    • Bogert, M.T.1    Breneman, H.C.2    Hand, W.F.3
  • 39
    • 0007331514 scopus 로고
    • Conversion of aromatic o‐aminothioamides to the corresponding pyrimidinethione derivatives with triethylorthoformate (either alone [18a,3c] or in the presence of acetic anhydride [18b]) has been reported
    • (1977) Tetrahedron , vol.23 , pp. 885
    • Taylor, E.C.1    McKillop, A.2    Vromen, S.3
  • 42
    • 0004135137 scopus 로고
    • Supplement I, 1st Ed, Wiley‐Interscience, New York
    • (1970) The Pyrimidines
  • 43
    • 84986434312 scopus 로고    scopus 로고
    • This method (which has received little, if any, attention to date) appears to be an attractive alternative to the conventional set of conversions hydroxy → chloro → amino in 4‐substituted pyrimidines [19] whenever the corresponding thione is readily accessible. The scope of this approach to amino derivatives from this and other fused pyrimidinethione systems is under investigation.
  • 49
    • 84986432960 scopus 로고    scopus 로고
    • Private communication from Dr. Joseph H. Burchenal.

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.