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.
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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
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
G Jones HM Fales WC Wildman (1963) Tetrahedron Lett 4 397 Occurrence Handle10.1016/S0040-4039(01)90645-8
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
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
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
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
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
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
V Prelog O Metzler (1946) Helv Chim Acta 29 1170 Occurrence Handle10.1002/hlca.19460290525 Occurrence Handle1:CAS:528:DyaH2sXit1yg
VP Litvinov (1999) Russ Chem Rev 68 737 Occurrence Handle10.1070/RC1999v068n09ABEH000533 Occurrence Handle1:CAS:528:DyaK1MXnsFCmsbk%3D
VP Litvinov LA Rodinovskaya YuA Sharanin AM Shestopalov A Senning (1992) Sulfur Reports 13 1 Occurrence Handle1:CAS:528:DyaK2cXivFygtLo%3D
VP Litvinov (1993) Phosphorus Sulfur Silicon 74 139 Occurrence Handle10.1080/10426509308038105 Occurrence Handle1:CAS:528:DyaK2cXhtlChsbo%3D
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
VP Litvinov (2006) Russ Chem Rev 75 645 Occurrence Handle10.1070/RC2006v075n07ABEH003619
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
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
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
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
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
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
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
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
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
VV Dotsenko SG Krivokolysko VP Litvinov EB Rusanov (2007) Doklady Chemistry 413 68 Occurrence Handle10.1134/S0012500807030032 Occurrence Handle1:CAS:528:DC%2BD2sXktVegsbs%3D
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
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
Howard EG (1956) Pat US 2733260; Avail URL: http://ep.espacenet.com/numberSearch?locale=en_ep
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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)
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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
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DOI: https://doi.org/10.1007/s00706-007-0784-1