Synthetic Organic Chemistry

1. Synthesis of Heterocyclic-Fused Furans and Dihydrofurans via (4+1)-Annulation with Ylide: Exploration of Unique Reactivity Behavior of α-Carbonyl Sulfoxonium Ylide, Dr. Gulshan Kumar, Mithilesh Nagpure, Vajja Krishna Rao, Prof. Sankar K. Guchhait, Eur.J. Org. Chem. 2022.


2. Annulation of conjugated azine-imine with a sulfoxonium ylide in a noncarbenoid route to synthesize multisubstituted imidazole-fused heterocycles, Sankar K. Guchhait, Meenu Saini, Viren J. Khivsara, and Santosh K. Giri, J. Org. Chem. 2021, 86, 5380–5387.


3. Chan-Lam N–arylation and C–H amination with heteroaromatic ring-NH: An approach to access extended-fused imidazo[1,2-a]-pyridines/pyrazines, Sankar K. Guchhait, Meenu Saini, New J. Chem., 2020, 44, 308.


4. Synthesis of polyfunctionalized pyrroles via a tandem reaction of Michael addition and intramolecular cyanide-mediated nitrile-to-nitrile condensation, Sankar K. Guchhait, Shailendra Sisodiya, Meenu Saini, Yesha V. Shah, Gulshan Kumar, Divine P Daniel, Neha Hura and Vikas Chaudhary, J. Org. Chem. 2018, 83, 5807–5815.


5. A nitrile-stabilized ammonium ylide as a masked C–C=N synthon in heterocyclization with amidine–imine: 3-component assembly to fused pyrimidine scaffolds, Sankar K. Guchhait, Meenu Saini, Divyani Sumkaria and Vikas Chaudhary Chem. Commun. 2017, 53, 6941–6944.


6. Synthesis of polysubstituted 2-aminoimidazoles via alkene diamination of guanidine with conjugated α-bromoalkenones, Sankar K. Guchhait, Neha Hura, and Archana P. Shah, J. Org. Chem. 2017, 82, 2745−2752. (The article was highlighted for its important insight in Synfacts 2017, 13, 0472.)


7. Pyridine C3-arylation of nicotinic acids accessible via a multicomponent reaction: an entry to all substituted-3,4-diarylated pyridines, Sankar K. Guchhait, Neha Hura, Kanchan Sinha and Dulal Panda, RSC Adv., 2017, 7, 8323–8331.


8. Oxidative dearomatization of indoles via Pd-catalyzed C–H oxygenation: An entry to C2- quaternary indolin-3-ones; Sankar K. Guchhait, Vikas Chaudhary, Vijay A. Rana, Garima Priyadarshani, Somnath Kandekar, Maneesh Kashyap, Org. Lett. 2016, 18, 1534-1537.


9. A reaction of 1,2-diamines and aldehydes with silyl cyanide as cyanide pronucleophile to access 2-aminopyrazines and 2-aminoquinoxalines, Sankar K. Guchhait, Garima Priyadarshani and Nikhil M. Gulghane, RSC Adv., 2016, 6, 56056–56063.


10. Pd-Catalyzed Ag(I)-promoted C3-arylation of pyrido[1,2‑a] pyrimidin-4-ones with bromo/iodoarenes, Guchhait, S. K.; Priyadarshani, G.; J. Org. Chem., 2015, 80, 8482−8488.


11. Synthesis of 2-arylpyridopyrimidinones, 6-aryluracils and tri- and tetra-substituted conjugated 7 alkenes via Pd-catalyzed enolic C–O bond activation-arylation, Guchhait, S. K.; Priyadarshani, G.; J. Org. Chem., 2015, 80, 6342−6349.


12. Desilylative activation of TMSCN in chemoselective Strecker–Ugi type reaction: functional fused imidazoles as building blocks as an entry route to annulated purines, Guchhait, S. K.; Chaudhary, V. Org. Biomol. Chem., 2014, 12, 6694-6705. (Cited in ChemInform, 2015, 46, DOI: 10.1002/chin.20150603)


13. α, β-Epoxy Esters in Multiple C–O/C–N Bond-Breaking/Formation with 2-Aminopyridines; Synthesis of Biologically Relevant (Z)-2-Methylene-imidazo[1,2-a]pyridin-3-ones, Guchhait, S. K.; Priyadarshani, G.; Hura, N. Synlett, 2014, 25, 1692-1696.

14. C−H Bond Functionalization Under Metalation−Deprotonation Process: Regioselective Direct Arylation of 3‑Aminoimidazo[1,2-a] pyrazine. Guchhait, S. K.; Kandekar, S.; Kashyap, M.; Taxak, N.; Bharatam, P. V. J. Org. Chem. 2012, 77, 8321-8328.

15. A chemoselective Ugi-type reaction in water using TMSCN as a functional isonitrile equivalent: generation of heteroaromatic molecular diversity, Guchhait, S. K.; Chaudhary, V.; Madaan, C. Org. Biomol. Chem. 2012, 10, 9271-9277. (Cited in ChemInform, 2013, 44, DOI: 10.1002/chin.201318035)

16. One-Pot Three-Step Cu-Catalyzed Five/Four-Component Reaction Constructs Polysubstituted Oxa/Thia-zolidin-2-imines, Madaan, C.; Saraf, S.; Priyadarshani, G.; Reddy, P. P.; Guchhait, S. K.; Kunwar, A. C.; Sridhar, B. Synlett, 2012, 23, 1955-1959.

17. Intramolecular oxidative coupling of 3-indolylarylketones with Pd (II)-catalysis under air: convenient access to indenoindolones, Guchhait, S. K.; Kashyap. M.; Kandekar, S. Tetrahedron Lett. 2012, 53, 3919.

18. CuSO4–Glucose for In Situ Generation of Controlled Cu(I)-Cu(II) Bi-catalysts: Multicomponent Reaction of Heterocyclic Azine and Aldehyde with Alkyne, and Cycloisomerization Towards Synthesis of N-Fused Imidazoles, Guchhait, S. K.; Chandgude, A. L.; Priyadarshani, G. J. Org. Chem. 2012, 77, 4438. (The work was highlighted in an organic chemistry portal, http://www.organicchemistry.org/abstracts/lit3/627.shtm)

19. Friedel–Crafts 3-(2-bromo) benzoylation of indoles and intramolecular direct arylation: An efficient route to indenoindolones, Guchhait, S. K.; Kashyap, M. Synthesis, 2012, 44, 619-627.

20. ZrCl4–Mediated regio- and chemoselective Friedel-Crafts acylation of Indole. Guchhait, S. K.; Kashyap, M.; Kamble, H. J. Org. Chem. 2011, 76, 4753-4758.

21. Groebke-Blackburn-Bienaymé multicomponent reaction in scaffold modification of adenine, guanine, and cytosine: Synthesis of aminoimidazole-condensed nucleobases. Guchhait, S. K.; Madaan, C. Tetrahedron Lett 2011, 52, 56-58.

22. Towards molecular diversity: dealkylation of tert-butyl amine in Ugi-type multicomponent reaction product establishes tert-butyl isocyanide as a useful convertible isonitrile. Guchhait, S. K.; Madaan, C. Org. Biomol. Chem. 2010, 8, 3631-3634.

23. Direct C-H bond arylation of (hetero)arenes with aryl and heteroarylboronic acids. Guchhait, S. K.; Kashyap, M.; Saraf, S. Synthesis 2010, 7, 1166-1170

24. A new process of multicomponent Povarov reaction-aerobic dehydrogenation: Synthesis of polysubstituted quinolines. Guchhait, S. K.; Madaan, C.; Jadeja, K. Tetrahedron Lett 2009, 50, 6861-6865.

25. A highly flexible and efficient Ugi-type multicomponent synthesis of versatile N-fused aminoimidazoles. Guchhait, S. K.; Madaan, C.; Thakkar, B. S. Synthesis 2009, 19, 3293-3300.

26. An efficient regioselective versatile synthesis of N-fused 2- and 3-aminoimidazoles via Ugi-type multicomponent reaction mediated by zirconium (IV) chloride in polyethylene glycol-400. Guchhait, S. K.; Madaan, C. Synlett 2009, 4, 628-632.

27. Synthesis and structure-activity relationships of metal-ligand complexes that potently inhibit cell migration. Beshir, A. B., Guchhait, S. K., José, A. G.; Fenteany, G. Bioorg. Med. Chem. Lett. 2008, 18, 498.

28. Convenient synthesis of α,β-unsaturated phosphonates via a Mizoroki-Heck reaction of arylboronic acids with diethyl vinylphosphonate. Kabalka, G. W.; Guchhait, S. K.; Naravane, A. Tetrahedron Lett. 2004, 45, 4685.

29. Convenient synthesis of α,β-unsaturated sulfones via a Mizoroki-Heck reaction of arylboronic acids with phenyl vinyl sulfones. Kabalka, G. W.; Guchhait, S. K. Tetrahedron Lett. 2004, 45, 4021.

30. Synthesis of diprotected monosubstituted hydrazine derivatives from tert-butyl carbazates and boronic acids. Kabalka, G. W.; Guchhait, S. K. Org. Lett. 2003, 5, 4129.

31. Synthesis of (E)- and (Z)-alkenylphosphonates using vinylboronates. Kabalka, G. W.; Guchhait, S. K. Org. Lett. 2003, 5, 729.

32. Zinc tetrafluoroborate–catalyzed Mannich-type reaction of aldimines and silyl enol ethers in aqueous medium. Ranu, B. C.; Samanta, S.; Guchhait, S. K. Tetrahedron 2002, 58, 983.

33. Selective reduction of terminal alkynes to alkenes by indium metal. Ranu, B. C.; Dutta, J.; Guchhait, S. K. J. Org. Chem. 2001, 66, 5624.

34. Indium metal as a reducing agent. Selective reduction of carbon-carbon double bond in highly activated conjugated alkenes. Ranu, B. C.; Dutta, J.; Guchhait, S. K. Org. Lett. 2001, 3, 2603.

35. Stereoselective reduction of aryl-substituted gem-dibromides to vinyl bromides by indium metal. Ranu, B. C.; Samanta, S.; Guchhait, S. K. J. Org. Chem. 2001, 66, 4102.

36. Construction of bicyclo[2.2.2]octanone systems by microwave-assisted solid phase Michael addition followed by Al2O3-mediated intramolecular aldolisation. An eco-friendly approach. Ranu, B. C.; Guchhait, S. K.; Ghosh; K.; Patra, A. Green Chemistry, 2000, 2, 5-6.

37. A convenient and efficient procedure for selective deprotection of acetates by titanium (IV) isopropoxides. Ranu, B. C.; Guchhait, S. K.; Saha, M. J. Indian Chem. Soc. 1999, 76, 547. (Special issue dedicated to Professor D. Nasipuri, India on the occasion of his 75th birth anniversary)

38. Catalytic hydrogen transfer reductions using ammonium formate. A review. Ranu, B. C.; Sarkar, A.; Guchhait; S. K.; Ghosh, K. J. Indian Chem. Soc. 1998, 75, 690-694. (Special issue dedicated to Professor Sukh Dev, India on the occasion of his 75th birthday)

39. Stereoselective debromination of aryl-substituted vic-dibromide with indium metal. Ranu, B. C.; Guchhait, S. K.; Sarkar, A. J. Chem. Soc., Chem. Commun., 1998, 2113.

40. Chemoselective hydrogenation of a, b-unsaturated sulfones and phosphonates via palladium assisted hydrogen transfer by ammonium formate. Ranu, B. C.; Guchhait, S. K.; Ghosh, K. J. Org. Chem. 1998, 63, 5250.