Skip to main content

Advertisement

SpringerLink
Log in

An efficient synthesis of structurally diverse 2-methyl-N-[(3-phenylamino)oxetan-3-yl]-2-propanesulfinamide derivatives under catalyst free conditions

  • Original Paper
  • Published:
Chemical Papers Aims and scope Submit manuscript

Abstract

A convenient and straightforward synthesis of structurally diverse 2-methyl-N-[(3-phenylamino)oxetan-3-yl]-2-propanesulfinamide derivatives from 3-oxetan-3-tert-butylsulfinimine and substituted aromatic amines in methanol at 60 °C temperature is described. The corresponding diaminooxetane derivatives are obtained in good to excellent yield under optimized reaction conditions. The method presented herein was found to be advantageous for diaminooxetane derivatives as emerging building block for future drug discovery. The title diaminooxetanes should be considered as bioisosteric to isopropylidenediamines and urea derivatives rather than to gem-dimethyl and carbonyl groups, respectively.

Graphical abstract

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

Fig. 1
Fig. 2
Scheme 1
Scheme 2

Similar content being viewed by others

References

  • Berthelot M, Besseau F, Laurence C (1998) The hydrogen-bond basicity pKHB scale of peroxides and ethers. Eur J Org Chem. doi:10.1002/(SICI)1099-0690(199805)1998:5<925:AID-EJOC925>3.0.CO;2-F

    Google Scholar 

  • Besseau F, Lucon M, Laurence C, Berthelot M (1998) Hydrogen-bond basicity pKHB scale of aldehydes and ketones. J Chem Soc Perkin Trans 2:101–108. doi:10.1039/A704427E

    Article  Google Scholar 

  • Bull JA, Croft RA, Davis OA, Doran R, Morgan KF (2016) Oxetanes: recent advances in synthesis, reactivity and medicinal Chemistry. Chem Rev 116(19):12150–12233. doi:10.1021/acs.chemrev.6b00274

    Article  CAS  Google Scholar 

  • Burkhard JA, Wultschik G, Plancher JM, Roger-Evans M, Carreira EM (2013) Synthesis and stability of oxetane analogs of thalidomide and lenalidomide. Org Lett 15(17):4312–4315. doi:10.1021/ol401705a

    Article  CAS  Google Scholar 

  • Cavalli A, Poluzzi E, De Ponti F, Racanatini M (2002) Toward a pharmacophore for drugs inducing the long QT syndrome: insights from a CoMFA study of HERG K(+) channel blockers. J Med Chem 45(18):3844–3853. doi:10.1021/jm0208875

    Article  CAS  Google Scholar 

  • Cogan DA, Liu G, Ellman J (1999) The asymmetric synthesis of alpha, alpha-dibranched amines by the trimethylaluminum mediated 1,2-addition of organolithiums to tert-butanesulfinyl ketimines. J Am Chem Soc 121:268–269. doi:10.1021/ja983217q

    Article  CAS  Google Scholar 

  • Fischer H, Kansy M, Bur D (2000) CAFA: a Novel tool for the calculation of amphiphilic properties of charged drug molecules. Chimia 54(11):640–645

    CAS  Google Scholar 

  • Gholap SS (2016) Pyrrole: an emerging scaffold for construction of valuable therapeutic agents. Eur J Med Chem 110:13–31. doi:10.1016/j.ejmech.2015.12.017

    Article  CAS  Google Scholar 

  • Gholap SS, Bandgar BP, Chavan HV, Dhakane VD, Deshmukh UP (2014) An efficient and green method for the synthesis of [1,3]oxazine derivatives catalyzed by thiamine hydrochloride (VB1) in wateri C. R Chim 17(6):431–436. doi:10.1016/j.crci.2013.06.002

    Google Scholar 

  • Gholap SS, Dhakane VD, Gholap Sandip S (2012) Solid-supported dichloro[1,3,5]-triazine: a versatile synthetic auxiliary for direct synthesis of N-sulfonylamines from sulphonic acid and amine. Jordan J Chem 7(3):279–285

    CAS  Google Scholar 

  • Gholap SS, Gunjal N (2017) 2,4,6-Trichloro-1,3,5-triazine (TCT) mediated one pot direct synthesis of N-benzoylthioureas from carboxylic acids. Arabian J Chem 10:S2750–S2753. doi:10.1016/j.arabjc.2013.10.021

    Article  CAS  Google Scholar 

  • Gholap SS, Deshmukh UP (2013) Synthesis and in vitro antimicrobial screening of 3-cinnamoyl coumarin and 3-[3-(1H-indol-2-yl)-3-aryl-propanoyl]-2H-chromen-2-ones. Iran J Catal 3:171–176. http://ijc.iaush.ac.ir/article_4966.html. Accessed 29 Sept 2013

  • Gholap SS, Gunjal N (2016) Thiamine hydrochloride (Vit-B1): An optimized green alternative for the synthesis of polyhydroquinoline derivatives. Iran J Catal 8:6(2):147–152. http://ijc.iaush.ac.ir/article_13482.html. Accessed 10 Dec 2015

  • Hamzik PJ, Brubaker JD (2010) Reactions of oxetan-3-tert-butylsulfinimine for the preparation of substituted 3-aminooxetanes. Org Lett 12(5):1116–1119. doi:10.1021/ol100119e

    Article  CAS  Google Scholar 

  • Hashino H, Shimizu N, Shimida N, Takita T, Takeuchi T, Hoshino H (1987) Inhibition of infectivity of human immunodeficiency virus by a novel nucleoside, oxetanocin, and related compounds. Antibiot 40:1077–1078

    Article  Google Scholar 

  • Holan G (1971) Rational design of degradable insecticides. Nature (London) 232:644–647

    Article  CAS  Google Scholar 

  • Huang JM, Yokoyama R, Yang CS, Fukuyama Y (2000) Merrilactone A, a novel neurotrophic sesquiterpene dilactone from Illicium merrillianum. Tetrahedron Lett 41(32):6111–6114

    Article  CAS  Google Scholar 

  • Li C, Lee D, Graf TN, Phifer SS, Nakanishi Y, Burgess JP, Riswan R, Setyowati FM, Sarebi AM, Kroll DD, Kingborn AD, Wani MC, Oberlies NH (2005) A hexacyclic ent-trachylobane diterpenoid possessing an oxetane ring from Mitrephora glabra. Org Lett 7:5709–5712. doi:10.1021/ol052498l

    Article  CAS  Google Scholar 

  • Liu G, Cogan DA, Owens TD, Tang TP, Ellman J (1999) Synthesis of enantiomerically pure N-tert-butanesulfinyl imines (tert-butanesulfinimines) by the direct condensation of tert-butanesulfinamide with aldehydes and ketones. J Org Chem 64:1278–1284. doi:10.1021/jo982059i

    Article  CAS  Google Scholar 

  • Loh J, Carrison RW, York WS, Stacey G (2002) Bradyoxetin, a unique chemical signal involved in symbiotic gene regulation. Proc Natl Acad Sci USA 99:14446–14451. doi:10.1073/pnas.222336799

    Article  CAS  Google Scholar 

  • MacLaughlin M, Yazaki R, Fessard TC, Carreira EM (2014) Oxetanyl peptides: novel peptidomimetic modules for medicinal chemistry. Org Lett 16:4070–4073. doi:10.1021/ol501590n

    Article  Google Scholar 

  • Malapit CA, Howell AR (2015) Recent applications of oxetanes in the synthesis of heterocyclic compounds. J Org Chem 80(17):8489–8495. doi:10.1021/acs.joc.5b01255

    Article  CAS  Google Scholar 

  • Mayer W, Ciba-Geigy AG (1992) EP 92-810027

  • Norbeck DW, Kramer JB (1988) Nucleoside mimetics: their chemistry and biological properties. J Am Chem Soc 110:7217–7218

    Article  CAS  Google Scholar 

  • Omura S, Murata M, Imamura N, Iwai Y, Tanaka H, Furusaki A, Matsumoto T (1984) Oxetin, a new antimetabolite from an actinomycete. Fermentation, isolation, structure and biological activity. J Antibiot (Tokyo) 37:1324–1342

    Article  CAS  Google Scholar 

  • Seki JL, Shimida N, Takahashi K, Takita T, Takeuchi T, Hoshino H (1989) Inhibition of infectivity of HIV by a novel nucleoside, oxetanocin, and related compounds. Antimicrob Agents Chemother 33:773–775. doi:10.1128/AAC.33.5.773

    Article  CAS  Google Scholar 

  • Shimada N, Hasegawa S, Harada T, Tomisawa T, Fujji A, Takita T (1986) Selective inhibition of human cytomegalovirus replication by a novel nucleoside, oxetanocin G. J Antibiot 39:1623–1625

    Article  CAS  Google Scholar 

  • Soloway SB, Vogel P, Aubin le Drian CH, Powell JE (1986) DuPont de Nemours, E.I. and Co, US 86-916334

  • Stephan AF, Karki K, McDonald WS, Dorff PH, Dutra JK, DiRico KJ, Won A, Subramanyam C, Efremov IV, O’Donnell CJ, Nolan CE, Becker SL, Pustilnik LR, Sneed B, Sun H, Lu Y, Robshaw AE, Riddell D, O’Sullivan TJ, Sibley E, Capetta S, Atchison K, Hallgren AJ, Miller E, Wood A, Obach RS (2011) Metabolism-directed design of oxetane-containing arylsulfonamide derivatives as γ-secretase inhibitors. J Med Chem 54:7772–7783. doi:10.1021/jm200893p

    Article  Google Scholar 

  • Wani MC, Taylor HL, Wall ME, Coggon P, Mcphail AT (1971) Plant antitumor agents. VI. The isolation and structure of taxol, a novel antileukemic and antitumor agent from Taxus brevifolia. J Am Chem Soc 93:2325–2327

    Article  CAS  Google Scholar 

  • Wuitschik G, Carreira EM, Roger- Envans M, Muller K (2008) In: Gadamasetti K, Braish T (eds) Oxetan-3-one: chemistry and synthesis in process chemistry in the Pharmaceutical Industry. Boca raton, CRC, pp 217–229

    Google Scholar 

  • Wuitschik G, Carreira EM, Wanger B, Fischer H, Parrilla I, Schuler F, Envans MR, Muller K (2010) J Med Chem 53:3227–3246. doi:10.1021/jm9018788

    Article  CAS  Google Scholar 

  • Wuitschik G, Rogers-Envans M, Muller K, Bucki A, Bernasconi M, Godel T, Fischer H, Wanger B, Parrilla I, Schuler F, Schneider J, Alker A, Schweinzer WB, Carreira EM (2006a) Spirocyclic oxetane: synthesis and properties. Angew Chem Int Ed 47:4512–4515. doi:10.1002/anie.200800450

    Article  Google Scholar 

  • Wuitschik G, Rogers-Envans M, Muller K, Fischer H, Wanger B, Schuler F, Polonchuk L, Carreira EM (2006b) Oxetane as promising modules in drug discovery. Angew Chem Int Ed 45:7736–7739. doi:10.1002/anie.200602343

    Article  CAS  Google Scholar 

  • Wuitschik G, PhD thesis, ETH, Zurich (2008) doi:10.3929/etz-a-005697432

Download references

Acknowledgements

Authors are thankful to Principal, P. V. P. College, Pravaranagar for providing necessary laboratory facilities and Dr. C. H. Gill for constant encouragement.

Author information

Authors and Affiliations

  1. Department of Chemistry and Research Center, Padmashri Vikhe Patil College of Arts, Science and Commerce, Pravaranagar (Loni Kd), Tal-Rahata, District-Ahmednagar, MS, 413713, India

    Sandip R. Ugale & Somnath S. Gholap

Authors
  1. Sandip R. Ugale
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Somnath S. Gholap
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Somnath S. Gholap.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOCX 4980 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Ugale, S.R., Gholap, S.S. An efficient synthesis of structurally diverse 2-methyl-N-[(3-phenylamino)oxetan-3-yl]-2-propanesulfinamide derivatives under catalyst free conditions. Chem. Pap. 71, 2435–2443 (2017). https://doi.org/10.1007/s11696-017-0237-1

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11696-017-0237-1

Keywords

Search

Navigation