Skip to main content
SpringerLink
Log in

The Synthesis of Cyclopenta[c]pyridine (2-Pyrindene) Derivatives

  • Published:
Monatshefte für Chemie - Chemical Monthly Aims and scope Submit manuscript

Summary.

Ethyl 2-(N-morpholinyl)cyclopent-1-ene-1-carboxylate reacted smoothly with cyanothioacetamide to give morpholinium 4-cyano-1-oxo-2,5,6,7-tetrahydro-1H-cyclopenta[c]pyridine-3-thiolate; the former when treated with N-benzyl-α-chloroacetamide gave either a S-alkyl derivative or cyclopenta[d]thieno[2,3-b]pyridine, depending on the reaction conditions. Under Mannich-type aminomethylation with primary amines and formaldehyde the above thiolate afforded derivatives of the previously unknown heterocyclic system, cyclopenta[g]pyrido[2,1-b][1,3,5]thiadiazine in 81–90% yields.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  • M Ohba R Izuta E Shimizu (2000) Tetrahedron Lett 41 10251 Occurrence Handle10.1016/S0040-4039(00)01824-4 Occurrence Handle1:CAS:528:DC%2BD3cXoslamtr4%3D

    Article  CAS  Google Scholar 

  • M Ohba R Izuta E Shimizu (2006) Chem Pharm Bull 54 63 Occurrence Handle10.1248/cpb.54.63 Occurrence Handle1:CAS:528:DC%2BD28Xjslehsb4%3D

    Article  CAS  Google Scholar 

  • G Jones HM Fales WC Wildman (1963) Tetrahedron Lett 4 397 Occurrence Handle10.1016/S0040-4039(01)90645-8

    Article  Google Scholar 

  • S Takamatsu Y-P Kim M Hayashi K Furuhata H Takayanagi K Komiyama HB Woodruff S Omura (1995) J Antibiot 48 1090 Occurrence Handle1:CAS:528:DyaK2MXovFOksr8%3D

    CAS  Google Scholar 

  • T Sunazuka T Zhi-Ming Y Harigaya S Takamatsu M Hayashi K Komiyama S Omura (1997) J Antibiot 50 274 Occurrence Handle1:CAS:528:DyaK2sXisFenuro%3D

    CAS  Google Scholar 

  • Djerassi C, Kutney JP, Shamma M, Shoolery JN, Johnson LF (1961) Chem Ind 210

  • C Djerassi JP Kutney M Shamma (1962) Tetrahedron 18 183 Occurrence Handle10.1016/0040-4020(62)80038-6 Occurrence Handle1:CAS:528:DyaF38XktFOjtrg%3D

    Article  CAS  Google Scholar 

  • T Sakan A Fujino F Murai Y Butsugan A Suzui (1959) Bull Chem Soc Jpn 32 315 Occurrence Handle10.1246/bcsj.32.315 Occurrence Handle1:CAS:528:DyaF3cXhslWntQ%3D%3D

    Article  CAS  Google Scholar 

  • L Guandalini S Dei F Gualtieri MN Romanelli S Scapecchi E Teodori K Varani (2002) Helv Chim Acta 85 96 Occurrence Handle10.1002/1522-2675(200201)85:1<96::AID-HLCA96>3.0.CO;2-7 Occurrence Handle1:CAS:528:DC%2BD38Xht1OjsLw%3D

    Article  CAS  Google Scholar 

  • Lavielle G, Hautefaye P, Pierre A, Atassi G, Hickman J, Cimetiere B (2002) Pat Appl US 2002/0077325

  • Hautefaye P, Atassi G, Pierre A, Cimetiere B, Hickman J, Lavielle G (2003) Pat US 6509345

  • Lavielle G, Hautefaye P, Pierre A, Atassi G, Hickman J, Cimetiere B (2003) Pat Appl US 2003/0105109; Avail URL: http://ep.espacenet.com/numberSearch?locale=en_ep

  • GP Shkil’ RS Sagitullin (1998) Chem Heterocycl Compd 34 507 Occurrence Handle10.1007/BF02290931 Occurrence Handle1:CAS:528:DyaK1MXmsFOgsg%3D%3D

    Article  CAS  Google Scholar 

  • V Prelog O Metzler (1946) Helv Chim Acta 29 1170 Occurrence Handle10.1002/hlca.19460290525 Occurrence Handle1:CAS:528:DyaH2sXit1yg

    Article  CAS  Google Scholar 

  • VP Litvinov (1999) Russ Chem Rev 68 737 Occurrence Handle10.1070/RC1999v068n09ABEH000533 Occurrence Handle1:CAS:528:DyaK1MXnsFCmsbk%3D

    Article  CAS  Google Scholar 

  • VP Litvinov LA Rodinovskaya YuA Sharanin AM Shestopalov A Senning (1992) Sulfur Reports 13 1 Occurrence Handle1:CAS:528:DyaK2cXivFygtLo%3D

    CAS  Google Scholar 

  • VP Litvinov (1993) Phosphorus Sulfur Silicon 74 139 Occurrence Handle10.1080/10426509308038105 Occurrence Handle1:CAS:528:DyaK2cXhtlChsbo%3D

    Article  CAS  Google Scholar 

  • Litvinov VP, Krivokolysko SG, Dyachenko VD (1999) Chem Heterocycl Compd: 509

  • VP Litvinov (1998) Russ Chem Bull Int Ed 47 2053 Occurrence Handle10.1007/BF02494257

    Article  Google Scholar 

  • VP Litvinov (2006) Russ Chem Rev 75 645 Occurrence Handle10.1070/RC2006v075n07ABEH003619

    Article  Google Scholar 

  • Litvinov VP, Promonenkov VK, Sharanin YuA, Shestopalov AM (1989) 3-Cyano-2(1H)-pyridinethiones and -selenones. In: Itogi Nauki I Tekhniki. Organicheskaya Khimiya, tom 17 (Results in Science and Technology. Organic Chemistry, Vol. 17). VINITI, Moscow, p 72 (in Russian)

  • Jie-Jack L (ed) (2005) Name Reactions in Heterocyclic Chemistry, Wiley Interscience, p 307

  • VP Litvinov YuA Sharanin VK Promonenkov LA Rodinovskaya AM Shestopalov VYu Mortikov (1984) Russ Chem Bull 33 1706 Occurrence Handle10.1007/BF00959212

    Article  Google Scholar 

  • VD Dyachenko YuA Sharanin AM Shestopalov LA Rodinovskaya AV Turov VP Litvinov VK Promonenkov (1990) Zhurn Obshch Khim (Russ J Gen Chem) 60 2384 Occurrence Handle1:CAS:528:DyaK3MXlsFyqu7g%3D

    CAS  Google Scholar 

  • VD Dyachenko AD Dyachenko AN Chernega (2004) Russ J Org Chem 40 397 Occurrence Handle10.1023/B:RUJO.0000034978.81993.bd Occurrence Handle1:CAS:528:DC%2BD2cXlslSgs7g%3D

    Article  CAS  Google Scholar 

  • For review see: Rodinovskaya LA, Promonenkov VK, Sharanin YuA, Litvinov VP, Shestopalov AM (1989) β-Enaminocarbonyl compounds in the synthesis of 3-cyano-2(1H)-pyridones. In: Itogi Nauki I Tekhniki Organicheskaya Khimiya, tom 17 (Results in Science and Technology. Organic Chemistry, Vol. 17). VINITI, Moscow, p 3 (in Russian)

  • G Stork A Brizzolara H Landesman Szmuszkovicz R Terrell (1963) J Am Chem Soc 85 207 Occurrence Handle10.1021/ja00885a021 Occurrence Handle1:CAS:528:DyaF3sXktVeis7w%3D

    Article  CAS  Google Scholar 

  • For reviews on the 1,3,5-thiadiazine chemistry, see: a) Smalley RK (1996) 1,3,5-Oxadiazines and 1,3,5-Thiadiazines. In: Boulton AJ (ed) Comprehensive Heterocyclic Chemistry II, Vol. 6. Elsevier, Oxford, UK, p 783; b) Moody CJ (1984) Polyoxa, Polythia and Polyaza Six-Membered Ring Systems. In: Katritzky AR, Rees CW (eds) Comprehensive Heterocyclic Chemistry, Vol. 3. Pergamon, Oxford, UK, p 1039

  • IM Orudjeva TE Efendiev SM Aliev (1981) Zhurn Org Knim (Russ J Org Chem USSR) 17 410

    Google Scholar 

  • VV Dotsenko SG Krivokolysko AN Chernega VP Litvinov (2003) Doklady Chemistry 389 IssueID4–6 92 Occurrence Handle10.1023/A:1023492608275 Occurrence Handle1:CAS:528:DC%2BD3sXjtVehtLY%3D

    Article  CAS  Google Scholar 

  • Dotsenko VV (2004) Cyanothioacetamide and its derivatives in the synthesis of ring-fused sulfur-containing pyridines. PhD Thesis, Zelinsky Institute of Organic Chemistry, Moscow, Russian Federation, 167 pp (In Russian)

  • VV Dotsenko SG Krivokolysko VP Litvinov (2007) Khim Geterotsikl Soedin (Chem Heterocycl Compd) 43 621

    Google Scholar 

  • VV Dotsenko SG Krivokolysko VP Litvinov (2005) Russ Chem Bull Int Ed 54 2692 Occurrence Handle10.1007/s11172-006-0177-3 Occurrence Handle1:CAS:528:DC%2BD28XjtlantLc%3D

    Article  CAS  Google Scholar 

  • VV Dotsenko SG Krivokolysko AN Chernega VP Litvinov (2007) Monatsh Chem 138 35 Occurrence Handle10.1007/s00706-006-0569-y Occurrence Handle1:CAS:528:DC%2BD2sXksl2j

    Article  CAS  Google Scholar 

  • VV Dotsenko SG Krivokolysko VP Litvinov EB Rusanov (2007) Doklady Chemistry 413 68 Occurrence Handle10.1134/S0012500807030032 Occurrence Handle1:CAS:528:DC%2BD2sXktVegsbs%3D

    Article  CAS  Google Scholar 

  • VV Dotsenko SG Krivokolysko VP Litvinov (2005) Chem Heterocycl Compd 41 1428 Occurrence Handle10.1007/s10593-006-0015-4 Occurrence Handle1:CAS:528:DC%2BD28XjsV2hsb4%3D

    Article  CAS  Google Scholar 

  • VV Dotsenko SG Krivokolysko VP Litvinov (2007) Monatsh Chem 138 489 Occurrence Handle10.1007/s00706-007-0620-7 Occurrence Handle1:CAS:528:DC%2BD2sXkvF2mtL0%3D

    Article  CAS  Google Scholar 

  • Howard EG (1956) Pat US 2733260; Avail URL: http://ep.espacenet.com/numberSearch?locale=en_ep

Download references

Author information

Authors and Affiliations

  1. “ChemEx” Laboratory, Vladimir Dal’ East Ukrainian National University, Lugansk, Ukraine

    Victor V. Dotsenko & Sergey G. Krivokolysko

  2. Russian Academy of Sciences, Zelinsky Institute of Organic Chemistry, Moscow, Russian Federation

    Victor P. Litvinov

Authors
  1. Victor V. Dotsenko
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Sergey G. Krivokolysko
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Victor P. Litvinov
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Victor V. Dotsenko.

Additional information

Victor P. Litvinov, was Deceased

Victor P. Litvinov, This paper is dedicated to the blessed memory of our colleague, Prof. Victor Petrovich Litvinov (Dec 24, 1932–Feb 26, 2007)

Rights and permissions

Reprints and permissions

About this article

Cite this article

Dotsenko, V., Krivokolysko, S. & Litvinov, V. The Synthesis of Cyclopenta[c]pyridine (2-Pyrindene) Derivatives. Monatsh Chem 139, 271–275 (2008). https://doi.org/10.1007/s00706-007-0784-1

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s00706-007-0784-1

Search

Navigation