Synlett 2015; 26(08): 1096-1100
DOI: 10.1055/s-0034-1380347
letter
© Georg Thieme Verlag Stuttgart · New York

Simple and Highly Efficient Synthesis of Indolo- and Pyrrolo[1,2-a]quinoxalines Promoted by Molecular Iodine

Mekala Ramamohan
a  Technology Development Centre, Custom Pharmaceutical Services, Dr. Reddy’s Laboratories Ltd, Bollaram Road, Miyapur, Hyderabad 500 04, India   Email: sarvaj@drreddys.com
b  Department of Chemistry, Jawaharlal Nehru Technological University Anantapur, Ananthapuramu 515 002, Andhra Pradesh, India
,
Regati Sridhar
a  Technology Development Centre, Custom Pharmaceutical Services, Dr. Reddy’s Laboratories Ltd, Bollaram Road, Miyapur, Hyderabad 500 04, India   Email: sarvaj@drreddys.com
,
Kamaraju Raghavendrarao
a  Technology Development Centre, Custom Pharmaceutical Services, Dr. Reddy’s Laboratories Ltd, Bollaram Road, Miyapur, Hyderabad 500 04, India   Email: sarvaj@drreddys.com
,
Naidu Paradesi
a  Technology Development Centre, Custom Pharmaceutical Services, Dr. Reddy’s Laboratories Ltd, Bollaram Road, Miyapur, Hyderabad 500 04, India   Email: sarvaj@drreddys.com
,
Kothapally Bannoth Chandrasekhar
b  Department of Chemistry, Jawaharlal Nehru Technological University Anantapur, Ananthapuramu 515 002, Andhra Pradesh, India
,
Sarva Jayaprakash*
a  Technology Development Centre, Custom Pharmaceutical Services, Dr. Reddy’s Laboratories Ltd, Bollaram Road, Miyapur, Hyderabad 500 04, India   Email: sarvaj@drreddys.com
› Author Affiliations
Further Information

Publication History

Received: 20 January 2015

Accepted after revision: 16 February 2015

Publication Date:
16 March 2015 (online)


Abstract

A simple and highly efficient strategy is developed for the synthesis of indolo- and pyrrolo[1,2-a]quinoxalines from the corresponding 2-(1H-indol/pyrrol-1-yl)anilines promoted by molecular iodine in good to excellent yields.

Supporting Information

 
  • References and Notes

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  • 24 Synthesis of Indolo- and Pyrrolo[1,2-a]quinoxalines; General Procedure: To a stirred solution of benzylamine (338 mg, 3.16 mmol) in MeCN (10 mL) was added iodine (800 mg, 3.16 mmol) followed by 1-(2-aminophenyl)pyrrole (250 mg, 1.58 mmol) at room temperature. The reaction mixture was heated to 80 °C and stirred for 5–8 h, with the progress of the reaction being monitored by TLC. Upon completion, the reaction mixture was allowed to cool to room temperature and excess iodine was quenched by the addition of sat. aq Na2S2O3. The mixture was extracted with ethyl acetate (10 mL), and the organic layer was dried over anhydrous Na2SO4, filtered, and the solvent was removed to give the crude product, which was further purified by silica-gel column chromatography (hexane–EtOAc, 4:1) to afford the desired product. 4-Phenylpyrrolo[1,2-a]quinoxaline (3a): Yield: 347 mg (90%); pale-yellow solid; mp 117–119 °C; IR (KBr): 3435, 3064, 2918, 1602, 1532, 1522, 1475, 1445, 1416, 1370, 1322, 1251, 1167, 1096, 1073, 912, 933, 752, 710, 688 cm–1; 1H NMR (400 MHz, CDCl3): δ = 6.87 (t, J = 3.0 Hz, 1 H), 6.98 (d, J = 3.2 Hz, 1 H), 7.55–7.42 (m, 5 H), 7.86 (d, J = 8.0 Hz, 1 H), 8.04–7.97 (m, 4 H); 13C NMR (100 MHz, CDCl3): δ = 108.6, 113.6, 114.0, 114.5, 125.2, 125.4, 127.1, 127.4, 128.5, 128.6, 129.7, 130.2, 136.2, 138.4, 154.4; MS: m/z = 245.2 [M + H]; HRMS (ESI): m/z [M + H] calcd. for C17H13N2: 245.1079; found: 245.1079.