Subscribe to RSS
DOI: 10.1055/s-0028-1088107
A New and Facile Synthesis of Thieno[2,3-b]indole Derivatives via Condensation of Isocyanide and Indolin-2-thiones
Publication History
Publication Date:
26 March 2009 (online)
![](https://www.thieme-connect.de/media/synlett/200907/lookinside/thumbnails/10.1055-s-0028-1088107-1.jpg)
Abstract
A new one-pot synthesis of thieno[2,3-b]indole ring systems is described. Condensation of cyclohexyl isocyanide with indolin-2-thiones yielded 3-cyclohexyaminomethylene-indolin-2-thiones, which upon reaction with α-halocarbonyl compounds produced the title compounds.
Key words
thieno[2,3-b]indole derivatives - isocyanide - thioamide
- 1
Gronowitz S. The Chemistry of Heterocyclic Compounds: Thiophene and Its Derivatives Vol. 44: Wiley; New York: 1991. -
2a
Kanbe K.Okamura M.Hattori S.Naganawa H.Hamada M.Okami Y.Takeuchi T. Biosci. Biotech. Biochem. 1993, 57: 632 -
2b
Kanbe K.Naganawa H.Nakamura KT.Okami Y.Takeuchi T. Biosci. Biotech. Biochem. 1993, 57: 636 - 3
Mezlova M.Aaron JJ.Adenier A.Maurel F.Chane-Ching K. J. Electroanal. Chem. 2005, 581: 93 - 4
Pedras MSC.Suchy M. Bioorg. Med. Chem. 2006, 14: 714 -
5a
Jakobsen P,Kanstrup A,Faarup P, andOlesen PH. inventors; US 5536721. -
5b
Jakobsen P,Kanstrup A,Faarup P,Olesen PH, andLundbech JM. inventors; US 5783575. -
6a
Cadogan JIG. Synthesis 1969, 11 -
6b
Sundberg RJ. J. Org. Chem. 1965, 30: 3604 -
7a
Scott TL.Soderberg BC. Tetrahedron Lett. 2002, 43: 1621 -
7b
Soderberg BC.Shriver JA. J. Org. Chem. 1997, 62: 5838 -
7c
Smitrovich JH.Davies IW. Org. Lett. 2004, 6: 533 -
7d
Appukkuttan P.Eycken EV.Dehaen W. Synlett 2005, 127 - 8
Engqvist R.Javaid A.Bergman J. Eur. J. Org. Chem. 2004, 2589 - 9
Butin AV.Tsiunchik FA.Abaev VT.Zavodnik VE. Synlett 2008, 1145 - 10
Majumdar KC.Alam S. J. Chem. Res. 2006, 5: 289 - 11
Jagodzinski ST. Chem. Rev. 2003, 103: 197 - 12
Saeidian H.Sadeghi A.Mirjafary Z.Moghaddam FM. Synth. Commun. 2008, 38: 2043 - 13
Dömling A. Chem. Rev. 2006, 106: 17 -
14a
Moghaddam FM.Mirjafary Z.Saeidian H.Javan MJ. Synlett 2008, 892 -
14b
Moghaddam FM.Saeidian H.Mirjafary Z.Sadeghi A. Lett. Org. Chem. 2007, 4: 576 -
14c
Moghaddam FM.Saeidian H.Mirjafary Z.Taheri S. J. Sulfur Chem. 2006, 27: 545 -
14d
Moghaddam FM.Zali Boinee H. Synlett 2005, 1612 -
14e
Moghaddam FM.Zali Boinee H. Tetrahedron 2004, 60: 6085 -
14f
Moghaddam FM.Zali Boinee H. Tetrahedron Lett. 2003, 44: 6253 -
16a
Scheeren JW.Ooms PHJ.Nivard RJF. Synthesis 1973, 149 -
16b
Vogel AI.Tatchell AR.Furnis BS.Hannaford AJ.Smith PWG. Vogel’s Textbook of Practical Organic Chemistry 4th ed: Longman; New York: 1978. p.815
References and Notes
Representative
Analytical Data
Compound 8b: ¹H
NMR (500 MHz, CDCl3): δ = 12.08
(m, 1 H), 8.06 (d, J = 13.71 Hz, 1 H),
7.43 (d, J = 7.55 Hz, 1 H), 7.21 (t,
J = 7.51 Hz, 1 H), 7.13-7.16
(m, 2 H), 3.77 (s, 3 H), 3.50-3.49 (m, 1 H), 2.11-2.07
(m, 2 H), 1.93-1.89 (m, 2 H), 1.69-1.59 (m, 3
H), 1.51-1.37 (m, 3 H) ppm. ¹³C
NMR (125 MHz, CDCl3): δ = 175.69
(C=S), 148.33 (CH), 139.86 (C), 127.68 (C), 123.16 (CH),
122.01 (CH), 114.61 (CH), 109.21 (CH), 106.58 (C), 58.76 (CH), 34.15
(CH2), 29.75 (CH3), 25.60 (CH2),
24.62 (CH2) ppm.
Compound 11a:
mp 285-287 ˚C. ¹H NMR (500
MHz, CDCl3/DMSO): δ = 11.33
(s, 1 H), 7.48 (s, 1 H), 7.35-7.30 (m, 3 H), 7.26 (d, J = 8.30
Hz, 2 H), 7.03 (d, J = 8.17 Hz, 1 H),
6.83 (t, J = 7.67 Hz, 1 H), 6.73 (t,
J = 7.51 Hz, 1 H) ppm. ¹³C
NMR (125 MHz, CDCl3/DMSO): δ = 187.19,
149.22, 143.10, 137.71, 135.26, 131.71, 130.50, 128.38, 126.04, 125.79,
123.71, 122.35, 120.55, 119.71, 112.16 ppm.
Compound 11b: mp 280-282 ˚C. ¹H
NMR (500 MHz, CDCl3/DMSO): δ = 11.33
(s, 1 H), 7.49 (s, 1 H), 7.40 (d, J = 8.36
Hz, 2 H), 7.35 (d, J = 7.73 Hz, 1 H),
7.10 (d, J = 8.36 Hz, 2 H), 7.04 (d,
J = 8.12 Hz, 1 H), 6.85 (t, J = 7.38
Hz, 1 H), 6.76 (t, J = 7.40 Hz, 1 H)ppm. ¹³C
NMR (125 MHz, CDCl3/DMSO): δ = 187.11,
149.21, 143.11, 137.50, 137.29, 135.33, 130.35, 128.77, 128.33,
125.80, 123.72, 122.37, 120.55, 119.71, 112.17 ppm.
Compound 17: mp 145-147 ˚C. ¹H
NMR (500 MHz, CDCl3): δ = 10.43
(s, 1 H), 8.38 (d, J = 7.95 Hz, 1 H),
7.48-7.47 (m, 2 H), 7.42-7.40 (m, 1 H), 4.07 (s,
3 H), 3.67 (s, 2 H) ppm. ¹³C NMR (125
MHz, CDCl3): δ = 186.02,
138.82, 136.22, 125.96, 125.84, 124.18, 122.13, 121.48, 115.69, 110.87,
31.17, 23.33 ppm.