CC BY ND NC 4.0 · SynOpen 2018; 02(01): 0050-0057
DOI: 10.1055/s-0036-1591932
paper
Copyright with the author

Synthesis of Sterically Protected Isoindoles from ortho-Phthalaldehyde

Michiyasu Nakao
a  Graduate School of Pharmaceutical Sciences, Tokushima University, Sho-machi, Tokushima 770-8505, Japan   Email: ssano@tokushima-u.ac.jp
,
Nanako Nishikiori
a  Graduate School of Pharmaceutical Sciences, Tokushima University, Sho-machi, Tokushima 770-8505, Japan   Email: ssano@tokushima-u.ac.jp
,
Akihito Nakamura
a  Graduate School of Pharmaceutical Sciences, Tokushima University, Sho-machi, Tokushima 770-8505, Japan   Email: ssano@tokushima-u.ac.jp
,
Murasaki Miyagi
a  Graduate School of Pharmaceutical Sciences, Tokushima University, Sho-machi, Tokushima 770-8505, Japan   Email: ssano@tokushima-u.ac.jp
,
Nao Shibata
a  Graduate School of Pharmaceutical Sciences, Tokushima University, Sho-machi, Tokushima 770-8505, Japan   Email: ssano@tokushima-u.ac.jp
,
Syuji Kitaike
a  Graduate School of Pharmaceutical Sciences, Tokushima University, Sho-machi, Tokushima 770-8505, Japan   Email: ssano@tokushima-u.ac.jp
,
Makoto Fukui
b  Department of Preventive Dentistry, Institute of Biomedical Sciences, Tokushima University Graduate School, 3-18-15, Kuramoto-cho, Tokushima 770-8504, Japan
,
Hiro-O Ito
b  Department of Preventive Dentistry, Institute of Biomedical Sciences, Tokushima University Graduate School, 3-18-15, Kuramoto-cho, Tokushima 770-8504, Japan
,
Shigeki Sano*
a  Graduate School of Pharmaceutical Sciences, Tokushima University, Sho-machi, Tokushima 770-8505, Japan   Email: ssano@tokushima-u.ac.jp
› Author Affiliations
Further Information

Publication History

Received: 05 December 2017

Accepted after revision: 15 January 2018

Publication Date:
20 February 2018 (online)

Abstract

o-Phthalaldehyde (OPA) reacts with O-protected tris(hydroxyalkyl)aminomethanes in the presence of 1-propanethiol to afford a novel class of stable isoindoles. Steric protection provided by the bulkiness of C 3-symmetric primary amines derived from tris(hydroxymethyl)aminomethane could be significant for the stabilization of 1-alkylthio-2-alkyl-substituted isoindoles derived from OPA. A plausible reaction mechanism is proposed to explain the formation of the isoindole and an isoindolin-1-one by-product.

Supporting Information

 
  • References

  • 1 Burford KN. Isoindole. In e-EROS Encyclopedia of Reagents for Organic Synthesis. Wiley; New York: 2015
    • 2a Roth M. Anal. Chem. 1971; 43: 880
    • 2b Zuman P. Chem. Rev. 2004; 104: 3217
    • 4a Gardner WS. Miller WH. Anal. Biochem. 1980; 101: 61
    • 4b Godel H. Graser T. Földi P. Pfaender P. Fürst P. J. Chromatogr. A 1984; 297: 49
    • 4c Lookhart GL. Jones BL. Cereal Chem. 1985; 62: 97
    • 4d Dorresteijn RC. Berwald LG. Zomer G. de Gooijer CD. Wieten G. Beuvery EC. J. Chromatogr. A 1996; 724: 159
    • 4e Lázaro de la Torre CA. Conte-Júnior CA. Braz. J. Vet. Res. Anim. Sci. 2013; 50: 430
    • 4f Borowczyk K. Chwatko G. Kubalczyk P. Jakubowski H. Kubalska J. Głowacki R. Talanta 2016; 161: 917
    • 4g Douša M. Pivoňková V. Sýkora D. J. Sep. Sci. 2016; 39: 3145
    • 5a Nakamura H. Matsumoto A. Tamura Z. Anal. Lett. 1982; 15: 1393
    • 5b Stobaugh JF. Repta AJ. Sternson LA. Garren KW. Anal. Biochem. 1983; 135: 495
    • 5c Jacobs WA. Leburg MW. Madaj EJ. Anal. Biochem. 1986; 156: 334
    • 5d Stobaugh JF. Repta AJ. Sternson LA. J. Pharm. Biomed. Anal. 1986; 4: 341
    • 5e García Alvarez-Coque MC. Medina Hernández MJ. Villanueva Camañas RM. Mongay Fernández C. Anal. Biochem. 1989; 178: 1
    • 5f Dai F. Burkert VP. Singh HN. Hinze WL. Microchem. J. 1997; 57: 166
    • 5g Heugebaert TS. A. Roman BI. Stevens CV. Chem. Soc. Rev. 2012; 41: 5626
    • 6a West R. Fink MJ. Michl J. Science 1981; 214: 1343
    • 6b Yoshifuji M. Shima I. Inamoto N. Hirotsu K. Higuchi T. J. Am. Chem. Soc. 1981; 103: 4587
    • 7a Okazaki R. West R. Adv. Organomet. Chem. 1996; 39: 231
    • 7b Power PP. Chem. Rev. 1999; 99: 3463
    • 7c Tokitoh N. Acc. Chem. Res. 2004; 37: 86
    • 7d Kira M. Iwamoto T. Adv. Organomet. Chem. 2006; 54: 73
    • 7e Mizuhata Y. Sasamori T. Tokitoh N. Chem. Rev. 2009; 109: 3479
    • 7f Wang Y. Robinson GH. Chem. Commun. 2009; 5201
    • 7g Fischer RC. Power PP. Chem. Rev. 2010; 110: 3877
    • 7h Scheschkewitz D. Chem. Lett. 2011; 40: 2
    • 7i Asay M. Sekiguchi A. Bull. Chem. Soc. Jpn. 2012; 85: 1245
    • 7j Sasamori T. Tokitoh N. Bull. Chem. Soc. Jpn. 2013; 86: 1005
    • 7k Yoshifuji M. Eur. J. Inorg. Chem. 2016; 607
    • 7l Yoshifuji M. Phosphorus, Sulfur, Silicon Relat. Elem. 2016; 191: 1452
    • 8a Sipos A. Török Z. Röth E. Kiss-Szikszai A. Batta G. Bereczki I. Fejes Z. Borbás A. Ostorházi E. Rozgonyi F. Naesens L. Herczegh P. Bioorg. Med. Chem. Lett. 2012; 22: 7092
    • 8b Sipos A. Máté G. Röth E. Borbás A. Batta G. Bereczki I. Kéki S. Jóna I. Ostorházi E. Rozgonyi F. Vanderlinden E. Naesens L. Herczegh P. Eur. J. Med. Chem. 2012; 58: 361
    • 9a Tonhauser C. Schüll C. Dingels C. Frey H. ACS Macro Lett. 2012; 1: 1094
    • 9b Schüll C. Nuhn L. Mangold C. Christ E. Zentel R. Frey H. Macromolecules 2012; 45: 5901
    • 10a Segura M. Sansone F. Casnati A. Ungaro R. Synthesis 2001; 2105
    • 10b Pasha A. Lin M. Tircsó G. Rostollan CL. Woods M. Kiefer GE. Sherry AD. Sun X. J. Biol. Inorg. Chem. 2009; 14: 421
    • 10c Chen Z. Hu W. Wang M. Wang L. Su G. Wang J. Carbohydr. Res. 2016; 429: 81
    • 10d Das R. Mukhopadhyay B. Tetrahedron Lett. 2016; 57: 1775
  • 11 Bundy GL. Pals DT. Lawson JA. Couch SJ. Lipton MF. Mauragis MA. J. Med. Chem. 1990; 33: 2276