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Synlett 2012(4): 557-558  
DOI: 10.1055/s-0031-1290354
LETTER
© Georg Thieme Verlag Stuttgart ˙ New York

A Synthesis of Highly Functionalized Pyrido[2,1-d][1,2,5]triazepines

Issa Yavari*, Gholamhossein Khalili, Fatemeh Sadeghizadeh
Department of Chemistry, Tarbiat Modares University, PO Box 14115-175, Tehran, Iran
Fax: +98(21)88006544; e-Mail: yavarisa@modares.ac.ir;
Further Information

Publication History

Received 19 October 2011
Publication Date:
13 February 2012 (online)

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Abstract

A synthesis of functionalized 1-(alkylamino)-4-aryl-2,3-dihydro-2-phenylpyrido[2,1-d][1,2,5]triazepines from the sequential reaction between pyridinium ylides, alkyl isocyanides, and 1-[chloro(aryl)methylene]-2-phenylhydrazines in CH2Cl2, in good yields, is described.

Keywords

pyrido[2,1-d][1,2,5]triazepine - hydrazonoyl chloride - alkyl isocyanide - pyridinium ylide - MCR

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15

General Procedure for the Synthesis of Compound 4
To a suspension of 1 (1 mmol) and isocyanide 2 (1 mmol) in CH2Cl2 (4 mL) was added Et3N (2 mmol) at r.t. After stirring for 20 h at r.t., hydrazonoyl chloride 3 (1 mmol) was added to the solution and stirred for 10 h. Subsequently, the solvent was evaporated, and the crude product was washed with EtOAc. The solid mixture was dissolved in CH2Cl2 (5 mL) and washed with two 3 mL portions of H2O, then dried (Na2SO4), and evaporated under reduced pressure.
Selected Spectroscopic Data for Compound 4a
Pale yellow powder, mp 148-150 ˚C, yield 0.34 g, 90%. IR (KBr): νmax = 3419 (NH), 1658, 1548, 1442 cm-¹. ¹H NMR (500 MHz, CDCl3): δ = 1.08 (3 H, t, ³ J = 7.1 Hz, Me), 1.21 (9 H, s, CMe3), 4.14-4.15 (2 H, m, CH2O), 6.91 (1 H, t, ³ J = 7.4 Hz, CH), 7.25-7.30 (4 H, m, 4 CH), 7.35-7.38 (2 H, m, 2 CH), 7.60-7.62 (2 H, d, ³ J = 7.7 Hz, 2 CH), 7.79 (1 H, t, ³ J = 6.4 Hz, CH), 7.93 (1 H, t, ³ J = 6.4 Hz, CH), 8.48 (1 H, t, ³ J = 8.1 Hz, CH), 8.73 (1 H, d, ³ J = 6.4 Hz, CH), 8.85 (1 H, d, ³ J = 6.4 Hz, CH), 9.59 (1 H, br s, NH), 10.32 (1 H, br s, NH) ppm. ¹³C NMR (125.7 MHz, CDCl3): δ = 13.9 (Me), 29.9 (CMe3), 54.7 (C), 60.3 (CH2O), 105.4 (C), 113.8 (2 CH), 121.0 (2 CH), 124.9 (C), 126.9 (CH), 127.1 (CH), 128.5 (CH), 128.7 (2 CH), 128.9 (2 CH), 130.9 (C), 135.0 (C), 143.8 (CH), 147.2 (CH), 147.5 (C), 148.3 (CH), 153.2 (C), 164.2 (C=O) ppm. MS: m/z (%) = 442 (4) [M+], 411 (75), 355 (77), 290 (28), 77 (100). Anal. Calcd (%) for C27H30N4O2 (442.24): C, 73.28; H, 6.83; N, 12.66. Found (%): C, 72.84; H, 6.51; N, 12.92.